US EPA

7462750 

Journal Article 

Regioselective Cp*Ir(III)-Catalyzed Allylic C-H Sulfamidation of Allylbenzene Derivatives 

Kazerouni, AM; Nelson, TAF; Chen, SW; Sharp, KR; Blakey, SB 

2019 

Yes 

Journal of Organic Chemistry
ISSN: 0022-3263
EISSN: 1520-6904 

American Chemical Society 

84 

20 

13179-13185 

English 

10.1021/acs.joc.9b01816 

In this study we report the development of the regioselective Cp*Ir(III)-catalyzed allylic C-H sulfamidation of allylbenzene derivatives, using azides as the nitrogen source. The reaction putatively proceeds through a Cp*Ir(III)-π-allyl intermediate and demonstrates exclusive regioselectivity for the branched position of the π-allyl. The reaction performs well on electron-rich and electron-deficient allylbenzene derivatives and is tolerant of a wide range of functional groups, including carbamates, esters, and ketones. The proposed mechanism for this reaction proceeds via C-N reductive elimination from a Cp*Ir(V) nitrenoid complex at the branched position of the π-allyl. © 2019 American Chemical Society. 

Catalysis; Ketones; Regioselectivity; Allylbenzene; Electron-deficient; Electron-rich; Nitrogen sources; Reductive elimination; Regio-selective; Iridium compounds; 2 [4 (tert butyl)phenyl] 1 tosyl 2,5 dihydro 1h pyrrole; 4 methyl n (1 phenylallyl)benzenesulfonamide; 4 methyl n (1 phenylbut 3 en 2 yl)benzenesulfonamide; 4 methyl n [1 (ortho tolyl)allyl]benzenesulfonamide; 4 methyl n [1 [4 (trifluoromethyl)phenyl]allyl]benzenesulfonamide; allylbenzene derivative; azide; benzene derivative; benzyl (1 phenylallyl)carbamate; carbamic acid derivative; carbon; hydrogen; methyl 4 [1 [(4 methylphenyl)sulfonamido]allyl]benzoate; n (1,3 diphenylallyl) 4 methylbenzenesulfonamide; n (6 bromohex 1 en 3 yl) 4 methylbenzenesulfonamide; n (hex 1 en 3 yl) 4 methylbenzenesulfonamide; n allyl n [1 [4 (tert butyl)phenyl]allyl] 4 methylbenzenesulfonamide; n cinnamyl 4 methylbenzenesulfonamide; n [1 (4 fluorophenyl)allyl] 4 methylbenzenesulfonamide; n [1 (4 methoxyphenyl)allyl] 4 methylbenzenesulfonamide; n [1 (benzo[d][1,3]dioxol 5 yl)allyl] 4 methylbenzenesulfonamide; n [1 [4 (tert butyl)phenyl]allyl] 4 methylbenzenesulfonamide; sulfonamide; unclassified drug; Article; catalysis; chemical reaction; deprotonation; electron; hydrogen bond; regioselectivity; ring closing metathesis; sulfamidation; synthesis