N-aryl or alkyl substituted sulfinamide compound and preparation method thereof

Abstract

The invention relates to N-aryl or alkyl substituted sulfinamide compounds and a preparation method thereof, and relates to the technical field of organic synthesis, the preparation method comprises the following steps: under the irradiation conditions of a photocatalyst and purple light with the wavelength of 365-375 nm, a compound 1 and a compound 2 are subjected to a reaction to obtain N-aryl or alkyl substituted sulfinamide compounds 3-31. According to the invention, carboxylic acid is used as a raw material, cheap ferric trichloride is used as a catalyst, and synthesis of various visible light induced N-aryl or alkyl substituted sulfonamide compounds is realized through a strategy of ligand-to-metal charge transfer. The preparation method disclosed by the invention has the advantages of cheap and easily available raw materials, mild reaction conditions, simplicity and convenience in operation, good substrate universality, easiness in amplification and the like, and industrial production and application can be realized.

Description

Technical Field

[0001] The present invention relates to the technical field of organic synthesis, and in particular to an N-aryl or alkyl substituted sulfenamide compound and a preparation method thereof. Background Art

[0002] N-aryl- or alkyl-substituted sulfenamides, an important class of nitrogen-containing compounds, are crucial building blocks in organic synthesis and medicinal chemistry. As crucial tetravalent sulfur derivatives, they have long served as versatile attachment points for constructing functional groups and are widely used in FDA-approved drugs and biological targets. Furthermore, chiral sulfenamides are often used as chiral auxiliary groups and ligands in asymmetric syntheses. Therefore, the synthesis of N-aryl- or alkyl-substituted sulfenamides holds significant theoretical and practical application value.

[0003] A small number of studies have been published on the synthesis of N-aryl or alkyl-substituted sulfenamides. For example, transition metal nickel or iron-catalyzed CN coupling reactions (Chem. Eur. J. 2022, 28, e202202190; Organometallics 2023, 42, 1704; Tetrahedron Lett 2019, 60, 151167). Another strategy is visible light-induced synthesis, but this requires functionalized substrates and metallic copper or iron reagents (ACS Catal. 2022, 12, 15334; Org. Lett. 2024, 26, 3679; Org. Biomol. Chem. 2024, 22, 348; Chem. Sci. 2023, 14, 13384; Org. Lett. 2024, 26, 3703). In addition, a small number of reports have been published on asymmetric syntheses catalyzed by organic small molecules and chiral phosphoric acid (Org. Lett. 2024, 23, 8499; ACS Catal. 2019, 9, 1525). Despite these achievements, the synthetic methods used in the literature still have some limitations, such as the need for noble metal catalysis, substrate prefunctionalization, and cumbersome operation procedures. Therefore, the development of green, efficient, and easy-to-operate synthetic methods remains of great significance. Summary of the Invention

[0004] In order to overcome the shortcomings of the above inventions, the present invention provides an N-aryl or alkyl substituted sulfenamide compound and a preparation method thereof. The present invention uses sulfenamide and carboxylic acid as substrates and uses inexpensive and readily available ferric chloride as a catalyst to achieve the synthesis of various N-aryl or alkyl substituted sulfenamide compounds and their derivatives.

[0005] The technical solutions of the present invention are as follows:

[0006] Under the conditions of photocatalysis and ultraviolet light irradiation, compound 1 and compound 2 generate N-aryl or alkyl substituted sulfenamide compounds and their derivatives 3-31.

[0007]

[0008] In a glove box, compound 1, compound 2, Et3N, and the photosensitizer FeCl3 (20 mol%) were weighed into an 8 mL sample vial. MeCN (2 mL) was added, and the PTFE cap was tightened. The sample vial was removed from the glove box and exposed to 365-375 nm blue light at room temperature for 24 hours. The target product 3-31 was obtained after isolation and purification.

[0009] Wherein R1 and R2 are both selected from any one of aryl and alkyl groups.

[0010] The structure of compound 3-31 is as follows:

[0011]

[0012] The wavelength of the violet light is 365-375nm.

[0013] The reaction solvent is N,N-dimethylformamide, methanol, acetonitrile, tetrahydrofuran and dimethyl sulfoxide.

[0014] The molar ratio of compound 1 to compound 2 is 1:1.5.

[0015] The reaction temperature is room temperature (20-30°C).

[0016] The N-aryl or alkyl substituted sulfenamide compounds prepared by the present invention are a very important class of organic synthesis intermediates and can be used to synthesize a variety of pharmaceutical synthesis intermediates through various conventional chemical transformations.

[0017] Compared with the prior art, the present invention has the following beneficial effects:

[0018] (1) The present invention uses cheap and readily available ferric chloride as a catalyst for the first time to achieve the visible light-induced synthesis of a variety of N-aryl or alkyl-substituted sulfenamide compounds.

[0019] (2) The preparation method of the present invention has the advantages of cheap and readily available raw materials, mild reaction conditions, simple operation, good substrate universality, and easy scale-up, and can be used for industrial production and application. DETAILED DESCRIPTION

[0020] To make the objectives, technical solutions, and advantages of the embodiments of the present invention more clear, the technical solutions in the embodiments of the present invention are clearly and completely described below. Obviously, the described embodiments are only part of the embodiments of the present invention, not all of them. All other embodiments obtained by ordinary technicians in this field based on the embodiments of the present invention without making any creative efforts are within the scope of protection of the present invention.

[0021] Unless otherwise specified, various raw materials, reagents, instruments and equipment used in the present invention can be purchased from the market or prepared by existing methods.

[0022] The present invention will be further described below in conjunction with specific examples. It should be understood that these examples are intended to illustrate the present invention only and are not intended to limit the scope of the invention. The experimental methods in the following examples where specific conditions are not specified are generally measured in accordance with national standards. If there are no corresponding national standards, then the methods are carried out in accordance with general international standards, conventional conditions, or the conditions recommended by the manufacturer.

[0023] Example 1-31:

[0024]

[0025] In a glove box, compound 1a (0.2 mmol), compound 2a (0.3 mmol), photosensitizer FeCl3 (20 mol%), and organic base Et3N (0.1 mmol) were weighed into an 8 mL sample vial. MeCN (2 mL) was added, and the PTFE cap was tightened. The sample vial was removed from the glove box and exposed to 40W 365-375 nm blue light at room temperature for 24 hours. After the reaction, the solvent was removed on a rotary evaporator to obtain the crude product. The target compound 3 was isolated and purified using petroleum ether / ethyl acetate in a volume ratio of 3:1 to obtain the target compound 3.

[0026] The NMR analysis data of compound 3 are as follows:

[0027] 1 H NMR (400MHz, CDCl3) δ: 7.24 (t, J = 7.6Hz, 2H), 7.02-6.98 (m, 3H), 5.78 (s, 1H), 1.32 (s, 9H).

[0028] 13 C NMR (101MHz, CDCl3) δ: 142.1, 129.3, 122.7, 118.1, 56.5, 22.4.

[0029] The catalysts, solvents, bases, light sources and yields of Examples 1 to 31 are shown in Table 1 below:

[0030]

[0031] Note: Superscript a indicates that unless otherwise specified, all reactions were carried out using 1a (0.2 mmol), 2a (0.15 mmol), iron catalyst (10 mmol%), base (1.5 mmol), and solvent (2 mL) at room temperature (20-30°C); Superscript b indicates the isolated yield of the product; Superscript c indicates Et3N (0.5 equivalent); Superscript d indicates 24 W blue light irradiation; Superscript e indicates 24 W white light irradiation; Superscript f indicates no iron catalyst; Superscript g indicates no Et3N; Superscript h indicates reaction in air; Superscript i indicates no light irradiation.

[0032] The experimental results are shown in Table 2.

[0033] Table 2

[0034]

[0035]

[0036]

[0037]

[0038]

[0039] The NMR analysis data of compound 4-31 are as follows:

[0040] The NMR analysis data of compound 4 are as follows:

[0041] 1 H NMR (400MHz, CDCl3) δ: 7.21 (t, J = 7.6Hz, 2H), 7.01-6.94 (m, 3H), 6.11 (s, 1H), 1.80 -1.71(m,1H),1.67-1.58(m,1H),1.27(s,3H),1.23(s,3H),1.00(t,J=7.6Hz,3H).

[0042] 13 C NMR (101MHz, CDCl3) δ: 142.3, 129.2, 122.4, 117.9, 59.9, 28.6, 18.9, 18.7, 7.9.

[0043] The NMR analysis data of compound 5 are as follows:

[0044] 1H NMR (400MHz, CDCl3) δ: 7.25 (t, J = 7.6Hz, 2H), 7.02-6.98 (m, 3H), 5.59 (s, 1H), 1.89-1.37 (m, 10H), 1.31 (s, 3H).

[0045] 13 C NMR (101MHz, CDCl3) δ: 142.2, 129.3, 122.7, 118.2, 60.0, 32.1, 30.6, 25.5, 21.8, 21.5, 15.6.

[0046] The NMR analysis data of compound 6 are as follows:

[0047] 1 H NMR (400MHz, CDCl3) δ: 7.22 (t, J = 7.6 Hz, 2H), 7.02-6.95 (m, 3H), 6.16 (s, 1H), 2.16-2.15 (m, 3H), 1.95-1.88 (m, 6H), 1.77-1.67 (m, 6H).

[0048] 13 C NMR (101MHz, CDCl3) δ: 142.4, 129.2, 122.4, 117.9, 58.2, 36.2, 34.6, 28.4.

[0049] The NMR analysis data of compound 7 are as follows:

[0050] 1 H NMR (400MHz, CDCl3) δ: 7.19 (t, J = 7.6Hz, 2H), 6.99-6.96 (m, 3H), 6.11 (s, 1H), 4.99(d,J=7.2Hz,1H),4.84(d,J=7.6Hz,1H),4.51-4.89(m,2H),1.65(s,3H).

[0051] 13 C NMR (101MHz, CDCl3) δ: 141.1, 129.5, 123.5, 118.6, 76.8, 76.5, 60.7, 16.1.

[0052] The NMR analysis data of compound 8 are as follows:

[0053] 1H NMR (400MHz, CDCl3) δ: 7.19 (t, J = 7.6 Hz, 2H), 7.14 (s, 1H), 7.01 (d, J = 8.0 Hz, 2H), 6. 96(t,J=7.2Hz,1H),3.14-3.03(m,1H),1.32(d,J=6.8Hz,3H),1.27(d,J=6.8Hz,3H).

[0054] 13 C NMR (101MHz, CDCl3) δ: 141.9, 129.2, 122.5, 117.8, 54.4, 16.1, 15.6.

[0055] The NMR analysis data of compound 9 are as follows:

[0056] 1 H NMR(400MHz, CDCl3)δ:7.24(t,J=7.6Hz,2H),7.05-6.97(m,3H),6.76(s,1H) ,3.79-3.71(m,1H),2.62-2.53(m,1H),2.31-2.16(m,3H),2.04-1.96(m,2H).

[0057] 13 C NMR (101MHz, CDCl3) δ: 141.5, 129.3, 122.7, 118.0, 56.3, 22.8, 21.4, 17.5.

[0058] The NMR analysis data of compound 10 are as follows:

[0059] 1 H NMR (400MHz, CDCl3) δ: 7.37 (s, 1H), 7.21 (t, J = 8.0Hz, 2H), 7.02 (d, J = 7.6Hz, 2H), 6.96 (t, J=7.6Hz,1H),3.52-3.44(m,1H),2.14-2.07(m,1H),1.96-1.85(m,2H),1.76-1.55(m,5H).

[0060] 13 C NMR (101MHz, CDCl3) δ: 141.9, 129.2, 122.4, 117.7, 63.9, 27.4, 27.2, 25.8, 25.7.

[0061] The NMR analysis data of compound 11 are as follows:

[0062] 1H NMR (400MHz, CDCl3) δ: 7.20 (t, J = 8.4Hz, 2H), 7.02-6.95 (m, 4H), 2.92-2.85 (m, 1H), 2.16- 2.13(m,1H),2.05-2.02(m,1H),1.88-1.81(m,2H),1.67-1.65(m,1H),1.56-1.22(m,5H).

[0063] 13 C NMR (101MHz, CDCl3) δ: 142.0, 129.3, 122.6, 117.9, 62.7, 26.5, 26.2, 25.4, 25.1, 25.0.

[0064] The NMR analysis data of compound 12 are as follows:

[0065] 1 H NMR(400MHz, CDCl3)δ:7.39(s,1H),7.23(t,J=7.6Hz,2H),7.04-6.98(m,3H),4.04-3.98(m,2H),3.34(td,J=11.2,2 .4Hz,1H),3.20(td,J=11.6,2.4Hz,1H),3.14-3.06(m,1H),2.01-1.97(m,1H),1.91-1.87(m,1H),1.85-1.64(m,2H).

[0066] 13 C NMR (101MHz, CDCl3) δ: 141.6, 129.4, 122.9, 117.9, 66.6, 66.5, 59.6, 27.0, 26.3.

[0067] The NMR analysis data of compound 13 are as follows:

[0068] 1 H NMR (400MHz, CDCl3) δ: 7.65 (s, 1H), 7.20 (t, J = 8.0Hz, 2H), 7.03-7.01 (m, 2H), 6.97 (t, J = 7.6Hz, 2H), 2.95 (dd, J = 13.2, 6.0Hz, 1H), 2.83 (dd, J=13.2, 8.0Hz, 1H), 2.15-2.08 (m, 1H), 1.05 (d, J=6.8Hz, 3H), 0.98 (d, J=6.4Hz, 3H).

[0069] 13C NMR (101MHz, CDCl3) δ: 141.5, 129.3, 122.6, 117.8, 64.3, 24.5, 22.1, 21.7.

[0070] The NMR analysis data of compound 14 are as follows:

[0071] 1 H NMR (400MHz, CDCl3) δ: 7.50 (s, 1H), 7.20 (t, J = 8.0Hz, 2H), 7.02-6.94 (m, 3H), 3.08 (d, J = 12.8Hz, 1H), 2.90 (d, J = 13.2Hz, 1H), 1.11 (s, 9H).

[0072] 13 C NMR (101MHz, CDCl3) δ: 141.3, 129.3, 122.6, 117.8, 70.1, 30.9, 29.7.

[0073] The NMR analysis data of compound 15 are as follows:

[0074] 1 H NMR (400MHz, CDCl3) δ: 7.32 (s, 1H), 7.23 (t, J = 7.6Hz, 2H), 7.03-6.97 (m, 3H), 3.07-2.95 (m, 2H), 1.68-1.53 (m, 3H), 0.91 (t, J = 6.4Hz, 6H).

[0075] 13 C NMR (101MHz, CDCl3) δ: 141.4, 129.4, 122.8, 118.1, 53.9, 31.8, 27.4, 22.2.

[0076] The NMR analysis data of compound 16 are as follows:

[0077] 1 H NMR (400MHz, CDCl3) δ: 7.55 (s, 1H), 7.21 (t, J = 7.6Hz, 2H), 7.03-6.95 (m, 3H), 2.96 (dd, J=13.2,6.0Hz,1H),2.82(dd,J=12.8,8.4Hz,1H),1.94-1.60(m,6H),1.32-0.99(m,5H).

[0078] 13C NMR (101MHz, CDCl3) δ: 141.5, 129.3, 122.6, 117.8, 63.0, 33.3, 32.8, 32.2, 25.9, 25.8, 29.6.

[0079] The NMR analysis data of compound 17 are as follows:

[0080] 1 H NMR (400MHz, CDCl3) δ: 7.62 (s, 1H), 7.20 (t, J = 7.6Hz, 2H), 7.01-6.96 (m, 3H), 5 .84-5.74(m,1H),5.13-5.06(m,2H),3.09(t,J=7.6Hz,2H),2.49-2.43(m,2H).

[0081] 13 C NMR (101MHz, CDCl3) δ: 141.4, 134.6, 129.3, 122.7, 118.0, 117.0, 54.5, 27.5.

[0082] The NMR analysis data of compound 18 are as follows:

[0083] 1 H NMR(400MHz, CDCl3)δ:7.40-7.34(m,5H),7.21(t,J=7.6Hz,2H),6.99(t,J=7.6Hz,1H ), 6.94 (d, J = 7.6Hz, 2H), 6.59 (s, 1H), 4.31 (d, J = 12.8Hz, 1H), 4.15 (d, J = 13.2Hz, 1H).

[0084] 13 C NMR (101MHz, CDCl3) δ: 141.0, 130.7, 129.4, 129.0, 128.9, 128.6, 123.3, 118.8, 61.3.

[0085] The NMR analysis data of compound 19 are as follows:

[0086] 1 H NMR(400MHz, CDCl3)δ:7.32-7.28(m,1H),7.19-7.11(m,5H),6.92(t,J=7.6Hz,1H),6.87-6.77(m,3H),4.24(d,J=12.8Hz,1H),4.08(d,J=12.8Hz,1H).

[0087] 13C NMR (101MHz, CDCl3) δ: 149.4, 140.7, 131.4, 130.3, 129.5, 128.9, 123.5, 122.9, 120.9, 118.7, 60.8.

[0088] 19 F NMR(376MHz, CDCl3)δ:-57.8(s,3F).

[0089] The NMR analysis data of compound 20 are as follows:

[0090] 1 H NMR(400MHz, CDCl3)δ:7.32-7.19(m,6H),6.98(t,J=7.6Hz,1H),6.87(d,J=7.6Hz,2H),5.47(s,1H),3.96 (q,J=7.2Hz,1H),2.51(d,J=7.2Hz,2H),1.95-1.85(m,1H),1.76(d,J=7.2Hz,3H),0.93(d,J=6.8Hz,6H).

[0091] 13 C NMR (101MHz, CDCl3) δ: 142.5, 141.0, 130.5, 129.5, 129.3, 129.2, 123.0, 118.6, 62.9, 45.1, 30.1, 22.4, 22.3, 15.3.

[0092] The NMR analysis data of compound 21 are as follows:

[0093] 1 H NMR (400MHz, CDCl3) δ: 7.22 (t, J = 7.6 Hz, 2H), 7.01-6.96 (m, 4H), 6.66 (d, J = 7.6 Hz, 1H), 6.59 (s, 1H), 5. 89(s,1H),3.93(t,J=5.6Hz,2H),2.30(s,3H),2.15(s,3H),1.95-1.76(m,4H),1.32(d,J=10.0Hz,6H).

[0094] 13 C NMR (101MHz, CDCl3) δ: 156.7, 142.1, 136.4, 130.3, 129.3, 123.4, 122.7, 120.8, 118.1, 111.9, 67.5, 59.4, 32.5, 23.8, 21.3, 19.6, 19.3, 15.7.

[0095] The NMR analysis data of compound 22 are as follows:

[0096] 1 H NMR (400MHz, CDCl3) δ: 7.28 (d, J = 8.4Hz, 2H), 6.95 (d, J = 8.8Hz, 2H), 5.61 (s ,1H),2.20-2.19(m,3H),1.97-1.89(m,6H),1.80-1.71(m,6H),1.29(s,9H).

[0097] 13 C NMR (101MHz, CDCl3) δ: 145.8, 139.5, 126.2, 118.2, 58.1, 38.7, 36.5, 36.3, 34.6, 34.2, 34.4, 28.5, 27.9.

[0098] The NMR analysis data of compound 23 are as follows:

[0099] 1 H NMR (400MHz, CDCl3) δ: 7.18 (d, J = 8.4Hz, 2H), 6.94 (d, J = 8.8Hz, 2H), 6.35 (s, 1H), 2.18-2.16 (m, 3H), 1.91-1.90 (m, 6H), 1.79-1.68 (m, 6H).

[0100] 13 C NMR (101MHz, CDCl3) δ: 141.2, 129.1, 127.5, 119.1, 58.5, 38.7, 36.4, 36.2, 34.6, 28.5, 27.9.

[0101] The NMR analysis data of compound 24 are as follows:

[0102] 1 H NMR (400MHz, CDCl3) δ: 7.12 (t, J = 7.6 Hz, 1H), 6.84-6.79 (m, 3H), 6.05 (s, 1H), 2.29 (s, 3H), 2.18-2.17 (m, 3H), 1.96-1.93 (m, 6H), 1.78-1.69 (m, 6H).

[0103] 13 C NMR (101MHz, CDCl3) δ: 142.2, 139.2, 129.1, 123.4, 118.7, 115.2, 58.1, 38.7, 36.5, 36.3, 34.6, 28.5, 27.9, 21.4.

[0104] The NMR analysis data of compound 25 are as follows:

[0105] 1 H NMR (400MHz, CDCl3) δ: 7.13 (t, J = 8.0 Hz, 1H), 7.05 (s, 1H), 6.94-6.88 (m, 2H), 6.49 (s, 1H), 2.17-2.15 (m, 3H), 1.91-1.90 (m, 6H), 1.77-1.67 (m, 6H).

[0106] 13 C NMR (101MHz, CDCl3) δ: 144.0, 134.9, 130.2, 122.3, 177.7, 115.7, 58.6, 38.7, 36.5, 36.2, 34.6, 28.5, 27.9.

[0107] The NMR analysis data of compound 26 are as follows:

[0108] 1 H NMR (400MHz, CDCl3) δ: 7.20 (s, 1H), 7.08 (d, J = 4.8Hz, 2H), 6.95-6.93 (m, 1H), 6.48 (s, 1H), 2.17-2.15 (m, 3H), 1.91-1.90 (m, 6H), 1.77-1.68 (m, 6H).

[0109] 13 C NMR (101MHz, CDCl3) δ: 144.1, 130.5, 125.2, 123.0, 120.6, 116.1, 58.6, 38.7, 36.4, 36.2, 34.6, 28.5, 27.9.

[0110] The NMR analysis data of compound 27 are as follows

[0111] 1 H NMR(400MHz, CDCl3)δ:7.15-7.13(m,3H),6.98-6.94(m,1H),5.47(s,1H),2.78(s,3H),2.21-2.20(m,3H),2.00-1.88(m,6H),1.81-1.72(m,6H).

[0112] 13 C NMR (101MHz, CDCl3) δ: 140.0, 130.7, 127.5, 127.0, 123.3, 119.0, 58.3, 38.6, 36.4, 36.3, 34.7, 28.5, 27.8, 17.7.

[0113] The NMR analysis data of compound 28 are as follows:

[0114] 1 H NMR (400MHz, CDCl3) δ: 7.34-7.27 (m, 2H), 7.19 (td, J = 7.6, 1.6Hz, 1H), 6.92 (td, J = 7. 6,1.6Hz,1H),6.23(s,1H),2.24-2.21(m,3H),2.00-1.90(m,6H),1.82-1.70(m,6H).

[0115] 13 C NMR (101MHz, CDCl3) δ: 138.7, 129.5, 127.8, 122.8, 122.6, 117.3, 58.7, 38.6, 36.4, 36.2, 34.5, 28.5, 27.8.

[0116] The NMR analysis data of compound 29 are as follows:

[0117] 1 H NMR (400MHz, CDCl3) δ: 7.49 (d, J = 8.0 Hz, 1H), 7.29-7.22 (m, 2H), 6.86 (t, J = 7. 6,1H),6.28(s,1H),2.24-2.22(m,3H),2.01-1.90(m,6H),1.83-1.71(m,6H).

[0118] 13 C NMR (101MHz, CDCl3) δ: 139.9, 132.7, 128.6, 123.3, 117.4, 113.1, 58.8, 38.6, 36.4, 36.2, 34.6, 28.5, 27.8.

[0119] The NMR analysis data of compound 30 are as follows:

[0120] 1 H NMR (400MHz, CDCl3) δ: 3.73 (q, J = 5.2Hz, 1H), 3.28 (d, J = 4.4Hz, 1H), 2.12-2.10 (m, 3H), 1.95-1.44 (m, 20H).

[0121] 13 C NMR (101MHz, CDCl3) δ: 56.8, 56.3, 38.7, 36.5, 36.3, 34.6, 33.2, 28.5, 27.9, 23.4, 23.1.

[0122] The NMR analysis data of compound 31 are as follows:

[0123] 1 H NMR(400MHz, CDCl3)δ:3.15-3.09(m,2H),2.09-2.07(m,3H),1.91-1.88(m,2H),1.79-1.61(m,14H),1.55-1.51(m,1H),1.28-1.09(m,5H).

[0124] 13 C NMR (101MHz, CDCl3) δ: 56.8, 53.9, 36.4, 35.2, 34.7, 34.0, 28.5, 25.5, 24.7, 24.4.

[0125] Various embodiments of the present invention may be presented in the form of a range; it should be understood that the description in a range format is only for convenience and brevity and should not be construed as an inflexible limitation on the scope of the invention; therefore, the range description should be considered to have specifically disclosed all possible subranges and single numerical values within the range. For example, the description of a range from 1 to 6 should be considered to have specifically disclosed subranges such as from 1 to 3, from 1 to 4, from 1 to 5, from 2 to 4, from 2 to 6, from 3 to 6, etc., as well as single numbers within the range, such as 1, 2, 3, 4, 5, and 6, regardless of the range. In addition, whenever a numerical range is indicated herein, it is intended to include any cited numeral (fractional or integer) within the indicated range.

[0126] The foregoing description is intended only to provide specific embodiments of the present invention, which will enable those skilled in the art to understand and implement the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the general principles defined herein may be implemented in other embodiments without departing from the spirit or scope of the present invention. Therefore, the present invention is not intended to be limited to the embodiments shown herein, but is intended to be accorded the widest scope consistent with the principles and novel features claimed herein.

Claims

1. A method for preparing an N-aryl or alkyl substituted sulfenamide compound, characterized in that: The preparation method comprises: Under the conditions of photocatalysis and irradiation of violet light with a wavelength of 365-375 nm, compound 1 and compound 2 react to obtain N-aryl or alkyl substituted sulfenamide compounds 3-31; The chemical reaction equation of the preparation method is as follows: Among them, R 1 and R 2 Substituted or unsubstituted aryl or alkyl groups are selected.

2. The method for preparing an N-aryl or alkyl substituted sulfenamide compound according to claim 1, wherein: The molar ratio of the compound 1 to the compound 2 is 1:1.

5.

3. The method for preparing an N-aryl or alkyl substituted sulfenamide compound according to claim 1, wherein: The reaction temperature is 20-30°C.

4. The method for preparing an N-aryl or alkyl substituted sulfenamide compound according to claim 1, wherein: The reaction solvent is at least one of N,N-dimethylformamide, methanol, acetonitrile, tetrahydrofuran and dimethyl sulfoxide.

5. The method for preparing N-aryl or alkyl substituted sulfenamide compounds according to claim 1, characterized in that: The compound 1 is selected from any one of the following compounds:

6. The method for preparing N-aryl or alkyl substituted sulfenamide compounds according to claim 1, characterized in that: The compound 2 is selected from any one of the following compounds:

7. The method for preparing an N-aryl or alkyl substituted sulfenamide compound according to any one of claims 1 to 6, characterized in that: The preparation method comprises the following steps: In a glove box, compound 1, compound 2, Et3N, and the photosensitizer FeCl3 (20 mol%) were weighed into an 8 mL sample vial. MeCN (2 mL) was added, and the PTFE cap was tightened. The sample vial was removed from the glove box and exposed to 365-375 nm blue light at room temperature for 24 hours. The target product 3-31 was obtained after isolation and purification.

8. An N-aryl or alkyl substituted sulfenamide compound, characterized in that: The N-aryl or alkyl substituted sulfenamide compound is prepared by the preparation method according to any one of claims 1 to 7.

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