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N-fluoro-1, 1'-binaphthyl-2, 2'-sulfimide and preparation method thereof
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A technology of sulfonylimide and binaphthyl, which is applied in the field of new electrophilic fluorinating reagents, can solve the problems that high-activity electrophilic fluorinating reagents cannot meet the development requirements, and achieve the effect of simple preparation and high reactivity
Active Publication Date: 2012-06-27
TIANJIN UNIV
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[0003] In the research of organic synthesis and medicinal chemistry, the introduction of fluorine atoms into organic compounds is one of the most active research fields in the world. A large number of new electrophilic fluorination reactions use fluorinating reagents, but limited high-activity electrophilic fluorination Reagents cannot meet current development requirements
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example 1
[0015] Example 1: Preparation of racemic N-fluoro-1,1'-binaphthyl-2,2'-sulfonimide (A):
[0016]
[0017] Under nitrogen protection, add 790 mg (2.0 mmol) of racemate 1,1'-binaphthyl-2,2'-sulfonimide and 252 mg (6.0 mmol) of anhydroussodiumfluoride to 50 mL of polytetrafluoroethylene 20 mL of dry acetonitrile was added to a stainless steel reactor with an inner sleeve, the temperature of the mixture was lowered to -30°C, nitrogen gas containing 5% fluorine gas was passed through for 2 hours, and then high-purity nitrogen gas was passed through for 2 hours. The reaction mixture was washed with sodiumsulfiteaqueous solution and extracted with ether. The organic phases were combined and dried by adding anhydrousmagnesiumsulfate. The solvent was evaporated and the product was recrystallized to obtain 702 mg of the target product with a yield of 85%. 1 H NMR (400MHz, CDCl 3 ), δppm: 7.20-7.35 (m, 4H, Ar), 7.50-7.62 (m, 2H, Ar), 7.95-8.00 (m, 2H, Ar), 8.10-8.22 (m, 4H, Ar)...
example 2
[0018] Example 2: Preparation of racemate N-fluoro-1,1'-binaphthyl-3,3'-diphenyl-2,2'-sulfonimide (B):
[0019]
[0020] In a method similar to Example 1, using 1,1'-binaphthyl-3,3'-diphenyl-2,2'-sulfonimide and anhydrouspotassium fluoride as raw materials, the reaction temperature is -40 ° C, Yield 83%. 1 H NMR (400MHz, CDCl 3 ), δppm: 7.20-7.50 (m, 14H, Ar), 7.72-7.95 (m, 2H, Ar), 8.12-8.25 (m, 4H, Ar); 19 F NMR (400MHz, CDCl 3 ), δppm-41.2(s).
example 3
[0021] Example 3: Racemate N-fluoro-1,1'-binaphthyl-3,3'-bis(3,5-bistrifluoromethylphenyl)-2,2'-sulfonimide (C ) preparation:
[0022]
[0023] A method similar to Example 1, using 1,1'-binaphthyl-3,3'-bis(3,5-bistrifluoromethylphenyl)-2,2'-sulfonylimide as raw material, reaction temperature The temperature was -35°C, and nitrogen gas containing 10% fluorine gas was passed through, and the yield was 90%. 1 H NMR (400MHz, CDCl 3 ), δppm: 7.20 (d, J=8.6Hz, 2H, Ar), 7.50-7.70 (m, 4H, Ar), 7.85 (s, 2H), 7.92 (s, 2H), 7.96 (s, 2H), 8.02-8.12 (m, 4H); 19 F NMR (400MHz, CDCl 3 ), δppm-39.8(s), -62.9(s), -63.0(s).
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Abstract
The invention relates to an N-fluoro-1, 1'-binaphthyl-2, 2'-sulfimide achiral and chiral fluorinated reagent and a preparation method thereof. Racemase or chiral 1, 1'-binaphthyl-2, 2'-sulfimide and a metalfluoride are added into an acetonitrile solution, and nitrogen containing 5-10% F2 is fed into the acetonitrile solution at the temperature of -30 DEG C to -40 DEG C. After full reaction, pure nitrogen is further fed to blow away unreacted fluoride. A solvent is evaporated to obtain the N-fluoro-1, 1'-binaphthyl-2, 2'-sulfimide fluorinated reagent. The preparation method of the fluorinated reagent is simple and high in reaction activity. In the studies of organic synthesis and pharmaceutical chemistry, fluorine atoms are introduced into organic compounds is one of most active research fields in the internationally. At present, a large amount of new electrophilic fluorination reactions need the fluorinated reagent, and limited high-activity electrophilic fluorinated reagents cannot meet the requirements of current development. Due to the high reaction activity, the fluorinated reagent is applied to the electrophilic fluorination reactions, thereby solving the very necessary and urgent problems at present.
Description
technical field [0001] The invention relates to a class of novel electrophilic fluorinating reagents, and in particular discloses a class of N-fluoro-1,1'-binaphthyl-2,2'-sulfonimide and a preparation method thereof. Background technique [0002] Electrophilic fluorination is a common chemical transformation to introduce fluorine atoms into organic compounds (J.-A. Ma, D. Cahard, Chem. Rev., 2008, 108, PR1-43). Neutral N-fluorosulfonimides are an important class of electrophilic fluorinating reagents with relatively mild reaction conditions. As early as 1988, E. Differding in the United States developed a class of neutral N-fluorosulfonamide fluorinating reagents (Tetrahedron Lett., 1988, 29, 6087 and US 5003074 (1991)) using natural camphor as raw materials. Subsequently, many research groups have developed many chiral electrophilic fluorinating reagents (Tetrahedron Lett.1993,34,3971; Chem.Pharm.Bull.1997,45,1085; JP 09,249,653 (1997); J.Org.Chem .1998,63,2273; J.Org.Che...
Claims
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