Transition-Metal-Free Intermolecular Amination of sp3 C-H Bonds with Sulfonamides

被引:125
作者
Fan, Renhua [1 ]
Li, Weixun [1 ]
Pu, Dongming [1 ]
Zhang, Li [1 ]
机构
[1] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China
基金
中国国家自然科学基金;
关键词
ACTIVATED METHYLENE-COMPOUNDS; VINYLIC HALOGEN SUBSTITUTION; POLYVALENT IODINE COMPOUNDS; COPPER-CATALYZED AMIDATION; RADICAL CYCLIZATION; ORGANOHYPERVALENT IODINE; INDUCED AZIRIDINATION; RUTHENIUM PORPHYRINS; AMIDYL RADICALS; MILD CONDITIONS;
D O I
10.1021/ol900090f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient transition-metal-free intermolecular benzylic amidation with sulfonamides is described. Various valuable nitrogen-containing compounds, including amines, beta-chloro amine, amino alcohol, alpha-, beta-amino ester, and N-sulfonyl imine, are generated from the preferential N-functionalization of saturated benzylic C-H bonds. The potential of this reaction system also lies in the fact it can be developed into an environmentally friendly intermolecular amidation process.
引用
收藏
页码:1425 / 1428
页数:4
相关论文
共 69 条
[1]   Amination of ethers using chloramine-T hydrate and a copper(I) catalyst [J].
Albone, DP ;
Challenger, S ;
Derrick, AM ;
Fillery, SM ;
Irwin, JL ;
Parsons, CM ;
Takada, H ;
Taylor, PC ;
Wilson, DJ .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (01) :107-111
[2]   Efficient copper-catalyzed benzylic amidation with anhydrous chloramine-T [J].
Bhuyan, Ranjana ;
Nicholas, Kenneth M. .
ORGANIC LETTERS, 2007, 9 (20) :3957-3959
[3]   Tandem radical decarboxylation-oxidation of amino acids:: A mild and efficient method for the generation of N-acyliminium ions and their nucleophilic trapping [J].
Boto, A ;
Hernández, R ;
Suárez, E .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (16) :4930-4937
[4]   Short and efficient synthesis of chiral furyl carbinols from carbohydrates [J].
Boto, Alicia ;
Hernandez, Dacil ;
Hernandez, Rosendo .
ORGANIC LETTERS, 2007, 9 (09) :1721-1724
[5]   INTRAMOLECULAR NITRENE C-H INSERTIONS MEDIATED BY TRANSITION-METAL COMPLEXES AS NITROGEN ANALOGS OF CYTOCHROME-P-450 REACTIONS [J].
BRESLOW, R ;
GELLMAN, SH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (22) :6728-6729
[6]   TOSYLAMIDATION OF CYCLOHEXANE BY A CYTOCHROME-P-450 MODEL [J].
BRESLOW, R ;
GELLMAN, SH .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (24) :1400-1401
[7]   Investigations in the transition metal catalyzed aziridination of olefins, amination, and other insertion reactions with Bromamine-T as the source of nitrene [J].
Chanda, BM ;
Vyas, R ;
Bedekar, AV .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (01) :30-34
[8]   Iminoiodanes and C-N bond formation in organic synthesis [J].
Dauban, P ;
Dodd, RH .
SYNLETT, 2003, (11) :1571-1586
[9]   Recent advances in catalytic intramolecular C-H aminations [J].
Davies, HML ;
Long, MS .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (23) :3518-3520
[10]   Recent advances in catalytic enantioselective intermolecular C-H functionalization [J].
Davies, Huw M. L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (39) :6422-6425