Method for synthesizing tetra-substituted olefin through carbon iodination of alkyne under catalysis of nickel

Abstract

The invention is applicable to the technical field of organic chemistry, and provides a method for synthesizing tetra-substituted olefin by carbon iodination of nickel-catalyzed alkyne, which comprises the following steps: dissolving asymmetric internal alkyne, aryl iodide, a nickel catalyst, a ligand, alkali, a boron reagent and an additive in an organic solvent to carry out trans-carbon iodination reaction of alkyne in a water-free and oxygen-free nitrogen atmosphere to obtain tetra-substituted olefin. And separating and purifying to obtain a trans-olefin product. According to the present invention, the cheap metal nickel catalyst is combined with the boron reagent to achieve the alkyne single selective synthesis of the tetra-substituted olefin, the reaction system has characteristics of good chemical selectivity, mild condition and high yield, the double conversion modules can achieve the configuration-maintained tetra-substituted olefin conversion, and the high synthesis application value is provided; the stereoselectivity and regioselectivity are good (as high as E: Zgt; 99 / : 1, rrgt; 20: 1), excellent functional group tolerance is achieved, and the highest yield can reach 90%.

Description

Technical Field

[0001] The invention belongs to the technical field of organic chemistry, and in particular relates to a method for synthesizing tetrasubstituted olefins through the carboniodination of alkynes catalyzed by nickel. Background Art

[0002] As an important structural unit, carbon-carbon double bonds have a wide range of applications in drug molecule design and functional material development. Taking tetrasubstituted olefin derivatives as an example, the breast cancer drug tamoxifen not only shows significant clinical efficacy, but also serves as a typical aggregation-induced luminescence emitter, attracting much attention in the field of fluorescent probe construction. By introducing a variety of aromatic rings or functional groups at the double bond site, the photophysical properties of the material can be precisely controlled, significantly expanding its application prospects in photovoltaic devices and optoelectronic systems. However, the modification of such structures is highly dependent on the precise control of the olefin stereoconfiguration. Currently, the synthesis of 1,2-trans disubstituted olefins mainly relies on free radical difunctionalization strategies, while carbon metallation methods with the same stereoselectivity are still rarely reported.

[0003] In recent years, significant progress has been made in the synthesis of alkenyl iodides from alkynes, primarily through strategies such as electrophilic iodination of alkynes, free radical-mediated iodine atom transfer, electrophilic halogenation of alkynyl tetracoordinate boron complexes-induced aromatic migration, and carbometallation. However, existing methods still have significant limitations: carbometallation mechanisms generally favor cis-addition, while 1,2-trans difunctionalization still primarily relies on free radical processes, and few reports have been published on stereoselective strategies based on carbometallation.

[0004] Therefore, it is of great significance to develop a structurally clear and modular synthesis method for tetrasubstituted olefins, which will provide an effective way to obtain olefin derivatives with clear stereoconfiguration and broad functional group compatibility. Summary of the Invention

[0005] The purpose of the embodiments of the present invention is to provide a method for synthesizing tetrasubstituted alkenes by nickel-catalyzed carboniodination of alkynes, aiming to solve the problems raised in the above background technology.

[0006] The embodiment of the present invention is achieved by providing a method for synthesizing tetrasubstituted olefins by nickel-catalyzed carboniodination of alkynes, the synthesis equation of which is shown below:

[0007]

[0008] The specific process includes the following:

[0009] In an anhydrous and oxygen-free nitrogen atmosphere, an asymmetric internal alkyne, an aryl iodide, a nickel catalyst, a ligand, a base, a boron reagent and an additive are dissolved in an organic solvent to carry out a trans-carbon iodination reaction of the alkyne, and a trans-olefin product is obtained after separation and purification;

[0010] Wherein, the molar amount of the aryl iodide is 1-2.5 times, more preferably 2.5 times, the molar amount of the asymmetric internal alkyne;

[0011] The molar amount of the nickel catalyst is 5-20% of the molar amount of the asymmetric internal alkyne, more preferably 10%;

[0012] The molar amount of the ligand is 5%-20% of the molar amount of the asymmetric internal alkyne, more preferably 10%;

[0013] The molar amount of the base is 0.5-2 times the molar amount of the asymmetric internal alkyne, more preferably 2 times;

[0014] The molar amount of the boron reagent is 0.5-2 times the molar amount of the asymmetric internal alkyne, more preferably 2 times;

[0015] The molar amount of the additive is 0.1-2 times the molar amount of the asymmetric internal alkyne, more preferably 2 times;

[0016] The reaction temperature is 40-60° C., and the reaction time is 1-24 h; more preferably 40° C., and the reaction time is 24 h.

[0017] Preferably, the asymmetric internal alkyne has the general structural formula R 1 -≡--R 2 , R 1 is trimethylsilyl, R 2 Any one selected from the following groups: hydrogen atom, chain alkyl, cycloalkyl, phenyl, alcohol alkyl, alkoxybenzene, ester benzene, thienyl, ester steroid.

[0018] Preferably, the general structural formula of the aryl iodide is IR 3 ,R 3 Any one selected from the following groups: phenyl, naphthyl, biphenyl, methoxybenzene, dimethoxybenzene, trimethoxybenzene, benzodioxanyl, methyl sulfide benzene, morpholinephenyl, phenol, acetophenone, methyl benzoate.

[0019] Preferably, the nickel catalyst is one or more of nickel bromide, bis(1,5-cyclooctadiene)nickel(0), ethylene glycol dimethyl ether nickel bromide, nickel acetate, nickel acetylacetonate, nickel(II) trifluoromethanesulfonate, bis(hexafluoroacetylacetonate)nickel(II) hydrate, and [1,1′-bis(diphenylphosphino)ferrocene]nickel dichloride, more preferably nickel acetylacetonate.

[0020] Preferably, the ligand is 2,2′-bipyridine, 4,4′-dimethoxy-2,2′-bipyridine, 2,2′-bipyridine-4,4′-dicarboxaldehyde, 4,4′-dinitro-2,2′-bipyridine, 4,4′-diamino-2,2′-bipyridine, 4,4′-dibromo-2,2′-bipyridine, 2,2′-bipyridine-4,4′-dicarboxylic acid methyl ester, 1,10-phenanthroline, 2,9 -dimethyl-1,10-phenanthroline, 3,4,7,8-tetramethyl-1,10-phenanthroline, 4,7-dimethoxy-1,10-phenanthroline, 4,7-diphenyl-1,10-phenanthroline, α,α,α,-terpyridine, 2,2′-biquinoline, 2-(4,5-dihydro-2-oxazolyl)quinoline or more, more preferably 4,4′-dimethoxy-2,2′-bipyridine.

[0021] Preferably, the base is one or more of sodium bicarbonate, sodium carbonate, sodium hydroxide, sodium methoxide, lithium methoxide, and lithium tert-butoxide, more preferably lithium methoxide.

[0022] Preferably, the boron reagent is pinacol diborate.

[0023] Preferably, the additive is one or more of 1,1′-diphenylethylene, trans-1,2-diphenylethylene, cis-1,2-diphenylethylene, and dimethyl fumarate, more preferably 1,1′-diphenylethylene.

[0024] Preferably, the organic solvent is one or more of tetrahydrofuran, 2-methyltetrahydrofuran, N,N-dimethylformamide, 1,4-dioxane, diethyl ether, ethylene glycol dimethyl ether, toluene, 1,2-dichloroethane, and chlorobenzene, more preferably chlorobenzene.

[0025] Preferably, the separation and purification uses column chromatography or thin layer chromatography, and the developing solvent used in the chromatography is petroleum ether or a mixture of petroleum ether and ethyl acetate, with the ratio of the two being 5:1-1:0.

[0026] The present invention provides a method for synthesizing tetrasubstituted alkenes by nickel-catalyzed carboniodination of alkynes. Under the conditions of the combined action of a nickel catalyst, a ligand, a base, a boron reagent, and an additive, the alkyne is activated by the boron reagent to in situ generate a nickel (0) species, which then reacts with the nickel (II) to generate a nickel (I) species to achieve oxidative addition, migration insertion, and isomerization processes, thereby generating trans-olefins with good yield and selectivity.

[0027] This method has mild reaction conditions, high yield and excellent selectivity. The catalysts, ligands, bases, boron reagents and solvents in the reaction conditions are all commercially available and do not require further synthesis. They are cheap and acceptable, the reaction operation is simple, and it is suitable for large-scale production. BRIEF DESCRIPTION OF THE DRAWINGS

[0028] Figure 1 This is the hydrogen spectrum of the olefin product prepared in Example 1 of the present invention;

[0029] Figure 2 This is the carbon spectrum of the olefin product prepared in Example 1 of the present invention;

[0030] Figure 3 This is the hydrogen spectrum of the olefin product prepared in Example 2 of the present invention;

[0031] Figure 4 This is the carbon spectrum of the olefin product prepared in Example 2 of the present invention;

[0032] Figure 5 This is the hydrogen spectrum of the olefin product prepared in Example 3 of the present invention;

[0033] Figure 6 This is the carbon spectrum of the olefin product prepared in Example 3 of the present invention;

[0034] Figure 7 This is the hydrogen spectrum of the olefin product prepared in Example 4 of the present invention;

[0035] Figure 8 This is the carbon spectrum of the olefin product prepared in Example 4 of the present invention;

[0036] Figure 9 This is the hydrogen spectrum of the olefin product prepared in Example 5 of the present invention;

[0037] Figure 10 This is the carbon spectrum of the olefin product prepared in Example 5 of the present invention. DETAILED DESCRIPTION

[0038] In order to make the purpose, technical solutions and advantages of the present invention more clearly understood, the present invention will be further described in detail below with reference to the accompanying drawings and embodiments. It should be understood that the specific embodiments described herein are only used to explain the present invention and are not intended to limit the present invention.

[0039] Transition metal-catalyzed coupling reactions provide an effective synthetic platform for constructing all-carbon-containing, sterically hindered tetrasubstituted alkenes. This strategy effectively addresses the challenges of regio- and stereoselectivity control through mechanism-guided design.

[0040] To this end, the embodiments of the present invention, based on the research foundation of transition metal catalysis, propose a stereodirecting group strategy, which precisely controls the stereochemistry of alkenyl metal intermediates by introducing directing groups into alkyne substrates. The key design is that the directing group must be removable so that it can be controllably removed in the subsequent functionalization process, thereby providing new ideas for the efficient construction of structurally diverse trans-tetrasubstituted monoiodine alkenes for the later transformation.

[0041] The specific implementation of the present invention is described in detail below with reference to specific embodiments.

[0042] Example 1: A tetrasubstituted olefin compound (E)-5-iodo-4-phenyl-5-(trimethylsilyl)pent-4-en-1-yl benzoate, the preparation method of which comprises the following steps:

[0043] In a glove box under nitrogen atmosphere, 5-(trimethylsilyl)pent-4-yn-1-ylbenzoate (0.4 mmol, 1.0 equiv), iodobenzene (1.0 mmol, 2.5 equiv), nickel acetylacetonate (Ni(acac)2, 10.3 mg, 0.04 mmol, 0.1 equiv), 4,4′-dimethoxy-2,2′-bipyridine (8.6 mg, 0.04 mmol, 0.1 equiv), lithium methoxide (LiOMe, 30.1 mg, 0.8 mmol, 2.0 equiv), Pinacol diboronate (B2pin2, 203.1 mg, 0.8 mmol, 2.0 equivalents), 1,1′-diphenylethylene (144.2 mg, 0.8 mmol, 2.0 equivalents) and chlorobenzene (PhCl, 2 mL) were stirred at 40°C under nitrogen for 24 hours and monitored by thin-layer chromatography (TLC) until the starting material was completely consumed. After the reaction, the mixture was filtered through silica gel, the solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain the trans-olefin product, as shown below:

[0044]

[0045] The total yield of the reaction was quantitative (73%), and the ratio of trans-cis olefin in the product was: E / Z = 92 / 8.

[0046] Its hydrogen and carbon spectra are as follows Figure 1 、 Figure 2 As shown;

[0047] (E)-5-iodo-4-phenyl-5-(trimethylsilyl)pent-4-en-1-yl benzoate: pale yellow oily liquid, 1 HNMR (400MHz, CDCl3) δ8.05(d,J=7.7Hz,2H),7.55(t,J=6.9Hz,1H),7.43(t,J=7.5Hz,2H),7.32(d,J=5.3Hz,3H ),7.12(d,J=6.0Hz,2H),4.32(t,J=6.4Hz,2H),2.94–2.86(m,2H),1.86(dt,J=14.1,6.7Hz,2H),-0.10(s,9H). 13C NMR (101MHz, CDCl3) δ166.46,158.87,141.58,132.76,130.27,129.55,128.32,128.23,128.14,127.68,112.29,64.22,44.50,25.94,0.81.

[0048] Example 2: A tetrasubstituted olefin compound (E)-5-iodo-4-(4-methoxyphenyl)-5-(trimethylsilyl)pent-4-en-1-yl benzoate, the preparation method of which comprises the following steps:

[0049] In a glove box under nitrogen atmosphere, 5-(trimethylsilyl)pent-4-yn-1-ylbenzoate (104.2 mg, 0.4 mmol, 1.0 equiv), 4-iodoanisole (280.1 mg, 1.0 mmol, 2.5 equiv), nickel acetylacetonate (Ni(acac)2, 10.3 mg, 0.04 mmol, 0.1 equiv), 4,4′-dimethoxy-2,2′-bipyridine (8.6 mg, 0.04 mmol, 0.1 equiv), lithium methoxide (LiOMe, 30.1 mg, 0.8 mmHg) were added in sequence to a 25 mL Schlenk tube equipped with a magnetic stirrer. To the reaction mixture were added diphenylethylene (144.2 mg, 0.8 mmol, 2.0 equivalents), 1,1′-diphenylethylene (144.2 mg, 0.8 mmol, 2.0 equivalents) and chlorobenzene (PhCl, 2 mL). The reaction system was stirred at 40° C. for 24 hours under nitrogen protection and monitored by thin layer chromatography (TLC) until the starting material was completely consumed. After the reaction, the mixture was filtered through silica gel, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the trans-olefin product, as shown below:

[0050]

[0051] The total yield of the reaction was quantitative (90%), and the ratio of trans-cis olefin in the product was: E / Z = 94 / 6.

[0052] Its hydrogen and carbon spectra are as follows Figure 3 、 Figure 4 As shown;

[0053] (E)-5-iodo-4-(4-methoxyphenyl)-5-(trimethylsilyl)pent-4-en-1-yl benzoate: white solid, 1H NMR (400MHz, CDCl3) δ8.12–7.98(m,2H),7.54(t,J=7.4Hz,1H),7.42(t,J=7.7Hz,2H),7.02(d,J=8.6Hz,2H),6.84( d,J=8.6Hz,2H),4.30(t,J=6.5Hz,2H),3.81(s,3H),2.86(dd,J=9.0,6.9Hz,2H),1.92–1.74(m,2H),-0.09(s,9H). 13 C NMR (101MHz, CDCl3) δ166.52,159.22,158.67,133.82,132.79,130.31,12 9.58,129.49,128.26,113.50,112.02,64.29,55.24,44.46,26.04,0.96.

[0054] Example 3: A tetrasubstituted olefin compound (E)-4-(4-hydroxyphenyl)-5-iodo-5-(trimethylsilyl)pent-4-en-1-yl benzoate, the preparation method of which comprises the following steps:

[0055] In a glove box under nitrogen atmosphere, 5-(trimethylsilyl)pent-4-yn-1-yl benzoate (104.2 mg, 0.4 mmol, 1.0 equiv), 4-iodophenol (220.1 mg, 1.0 mmol, 2.5 equiv), nickel acetylacetonate (Ni(acac)2, 10.3 mg, 0.04 mmol, 0.1 equiv), 4,4′-dimethoxy-2,2′-bipyridine (8.6 mg, 0.04 mmol, 0.1 equiv), lithium methoxide (LiOMe, 30.1 mg, 0.8 mmol, 2.5 equiv) were added in sequence to a 25 mL Schlenk tube equipped with a magnetic stirrer. 0 equivalent), pinacol diboronate (B2pin2, 203.1 mg, 0.8 mmol, 2.0 equivalent), 1,1′-diphenylethylene (144.2 mg, 0.8 mmol, 2.0 equivalent) and 1,4-dioxane (2 mL). The reaction system was stirred at 50° C. for 24 hours under nitrogen protection and monitored by thin layer chromatography (TLC) until the starting material was completely consumed. After the reaction, the mixture was filtered through silica gel, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to finally obtain the trans olefin product, as shown below:

[0056]

[0057] The total yield of the reaction was quantitative (73%), and the ratio of trans-cis olefin in the product was: E / Z = 92 / 8.

[0058] Its hydrogen and carbon spectra are as follows Figure 5 、 Figure 6 As shown;

[0059] (E)-4-(4-Hydroxyphenyl)-5-iodo-5-(trimethylsilyl)pent-4-en-1-yl benzoate:

[0060] White solid, 1 H NMR (400MHz, CDCl3) δ8.05(d,J=7.5Hz,2H),7.55(t,J=7.2Hz,1H),7.43(t,J=7.6Hz,2H),6.96(d,J=8.2Hz,2H),6.82 (d,J=8.3Hz,2H),6.43(s,1H),4.32(t,J=6.3Hz,2H),2.95–2.77(m,2H),1.84(dt,J=14.0,6.5Hz,2H),-0.08(s,9H). 13 C NMR (101MHz, CDCl3) δ167.14,158.56,155.65,133.55,133.01,129.98,129.60,128.32,115.06,112.05,64.59,44.35,25.93,0.95.

[0061] Example 4: A tetrasubstituted olefin compound (E)-4-(1-iodo-1-(trimethylsilyl)hex-1-en-2-yl)phenol, the preparation method of which comprises the following steps:

[0062] In a glove box under nitrogen atmosphere, 1-hexyn-1-yltrimethylsilane (61.7 mg, 0.4 mmol, 1.0 equiv), 4-iodophenol (220.1 mg, 1.0 mmol, 2.5 equiv), nickel acetylacetonate (Ni(acac)2, 10.3 mg, 0.04 mmol, 0.1 equiv), 4,4′-dimethoxy-2,2′-bipyridine (8.6 mg, 0.04 mmol, 0.1 equiv), lithium methoxide (LiOMe, 30.1 mg, 0.8 mmol, 2.0 equiv), Pinacol diboronate (B2pin2, 203.1 mg, 0.8 mmol, 2.0 equivalents), 1,1′-diphenylethylene (144.2 mg, 0.8 mmol, 2.0 equivalents) and 1,4-dioxane (2 mL) were stirred at 50°C under nitrogen for 24 hours and monitored by thin-layer chromatography (TLC) until the starting material was completely consumed. After the reaction, the mixture was filtered through silica gel, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the trans-olefin product, as shown below:

[0063]

[0064] The total yield of the reaction was quantitative (84%), and the ratio of trans-cis olefin in the product was: E / Z = 92 / 8.

[0065] Its hydrogen and carbon spectra are as follows Figure 7 、 Figure 8 As shown;

[0066] (E)-4-(1-iodo-1-(trimethylsilyl)hex-1-en-2-yl)phenol: yellow transparent liquid, 1 HNMR(400MHz, CDCl3) δ6.94(d,J=8.5Hz,2H),6.79(d,J=8.5Hz,2H),5.52(s,1H) ,2.66(t,J=7.4Hz,2H),1.38–1.28(m,4H),0.87(t,J=6.6Hz,3H),-0.10(s,9H). 13 C NMR (101MHz, CDCl3) δ160.14,155.00,134.66,129.72,114.93,110.95,47.77,28.89,22.54,14.05,1.07.

[0067] Example 5: A tetrasubstituted olefin compound (E)-4-(1-cyclopropyl-2-iodo-2-(trimethylsilyl)vinyl)phenol, the preparation method of which comprises the following steps:

[0068] In a glove box under nitrogen atmosphere, (cyclopropylethynyl)trimethylsilane (55.3 mg, 0.4 mmol, 1.0 equiv), 4-iodophenol (220.1 mg, 1.0 mmol, 2.5 equiv), nickel acetylacetonate (Ni(acac)2, 10.3 mg, 0.04 mmol, 0.1 equiv), 4,4′-dimethoxy-2,2′-bipyridine (8.6 mg, 0.04 mmol, 0.1 equiv), lithium methoxide (LiOMe, 30.1 mg, 0.8 mmol, 2.0 equiv), Pinacol diboronate (B2pin2, 203.1 mg, 0.8 mmol, 2.0 equivalents), 1,1′-diphenylethylene (144.2 mg, 0.8 mmol, 2.0 equivalents) and 1,4-dioxane (2 mL) were stirred at 50°C under nitrogen for 24 hours and monitored by thin-layer chromatography (TLC) until the starting material was completely consumed. After the reaction, the mixture was filtered through silica gel, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the trans-olefin product, as shown below:

[0069]

[0070] The total yield of the reaction was quantitative (66%), and the ratio of trans-cis olefin in the product was: E / Z = 93 / 7.

[0071] Its hydrogen and carbon spectra are as follows Figure 9 、 Figure 10 As shown;

[0072] (E)-4-(1-cyclopropyl-2-iodo-2-(trimethylsilyl)vinyl)phenol: white solid, 1 H NMR(400MHz, CDCl3)δ6.80(d,J=8.4Hz,2H),6.74(d,J=8.4Hz,2H),5.50–5.24(m,1H ), 2.34(tt,J=8.2,5.2Hz,1H),0.73–0.66(m,2H),0.24–0.18(m,2H),-0.14(s,9H). 13 C NMR (101MHz, CDCl3) δ159.25,155.04,130.88,130.27,114.57,111.29,26.81,5.84,0.89.

[0073] The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention. Any modifications, equivalent substitutions and improvements made within the spirit and principles of the present invention should be included in the scope of protection of the present invention.

Claims

1. A method for synthesizing tetrasubstituted olefins by nickel-catalyzed carboniodination of alkynes, characterized in that: Its synthesis formula is as follows: The specific process includes the following: In an anhydrous and oxygen-free nitrogen atmosphere, an asymmetric internal alkyne, an aryl iodide, a nickel catalyst, a ligand, a base, a boron reagent and an additive are dissolved in an organic solvent to carry out a trans-carbon iodination reaction of the alkyne, and a trans-olefin product is obtained after separation and purification; Wherein, the molar amount of the aryl iodide is 1-2.5 times the molar amount of the asymmetric internal alkyne; The molar amount of the nickel catalyst is 5-20% of the molar amount of the asymmetric internal alkyne; The molar amount of the ligand is 5%-20% of the molar amount of the asymmetric internal alkyne; The molar amount of the base is 0.5-2 times the molar amount of the asymmetric internal alkyne; The molar amount of the boron reagent is 0.5-2 times the molar amount of the asymmetric internal alkyne; The molar amount of the additive is 0.1-2 times the molar amount of the asymmetric internal alkyne; The reaction temperature is 40-60° C., and the reaction time is 1-24 h.

2. The method for synthesizing tetrasubstituted olefins by nickel-catalyzed carboiodination of alkynes according to claim 1, characterized in that: The general structural formula of the asymmetric internal alkyne is R 1 -≡--R 2 , R 1 is trimethylsilyl, R 2 Any one selected from the following groups: hydrogen atom, chain alkyl, cycloalkyl, phenyl, alcohol alkyl, alkoxybenzene, ester benzene, thienyl, ester steroid.

3. The method for synthesizing tetrasubstituted olefins by nickel-catalyzed carboiodination of alkynes according to claim 1, characterized in that: The general structural formula of the aryl iodide is IR 3 ,R 3 Any one selected from the following groups: phenyl, naphthyl, biphenyl, methoxybenzene, dimethoxybenzene, trimethoxybenzene, benzodioxanyl, methyl sulfide benzene, morpholinephenyl, phenol, acetophenone, methyl benzoate.

4. The method for synthesizing tetrasubstituted olefins by nickel-catalyzed carboiodination of alkynes according to claim 1, characterized in that: The nickel catalyst is one or more of nickel bromide, bis(1,5-cyclooctadiene)nickel(0), ethylene glycol dimethyl ether nickel bromide, nickel acetate, nickel acetylacetonate, nickel(II) trifluoromethanesulfonate, bis(hexafluoroacetylacetonate)nickel(II) hydrate, and [1,1′-bis(diphenylphosphino)ferrocene] nickel dichloride.

5. The method for synthesizing tetrasubstituted olefins by nickel-catalyzed carboiodination of alkynes according to claim 1, characterized in that: The ligand is one or more of 2,2′-bipyridine, 4,4′-dimethoxy-2,2′-bipyridine, 2,2′-bipyridine-4,4′-dicarboxaldehyde, 4,4′-dinitro-2,2′-bipyridine, 4,4′-diamino-2,2′-bipyridine, 4,4′-dibromo-2,2′-bipyridine, 2,2-bipyridine-4,4′-dicarboxylic acid methyl ester, 1,10-phenanthroline, 2,9-dimethyl-1,10-phenanthroline, 3,4,7,8-tetramethyl-1,10-phenanthroline, 4,7-dimethoxy-1,10-phenanthroline, 4,7-diphenyl-1,10-phenanthroline, α,α,α,-terpyridine, 2,2′-biquinoline, and 2-(4,5-dihydro-2-oxazolyl)quinoline.

6. The method for synthesizing tetrasubstituted olefins by nickel-catalyzed carboiodination of alkynes according to claim 1, characterized in that: The base is one or more of sodium bicarbonate, sodium carbonate, sodium hydroxide, sodium methoxide, lithium methoxide, and lithium tert-butoxide.

7. The method for synthesizing tetrasubstituted olefins by nickel-catalyzed carboiodination of alkynes according to claim 1, characterized in that: The boron reagent is pinacol diboron.

8. The method for synthesizing tetrasubstituted alkenes by nickel-catalyzed carboiodination of alkynes according to claim 1, characterized in that: The additive is one or more of 1,1′-diphenylethylene, trans-1,2-diphenylethylene, cis-1,2-diphenylethylene, and dimethyl fumarate.

9. The method for synthesizing tetrasubstituted olefins by nickel-catalyzed carboiodination of alkynes according to claim 1, characterized in that: The organic solvent is one or more of tetrahydrofuran, 2-methyltetrahydrofuran, N,N-dimethylformamide, 1,4-dioxane, diethyl ether, ethylene glycol dimethyl ether, toluene, 1,2-dichloroethane, and chlorobenzene.

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