Palladium-Catalyzed Direct Arylation of C(sp3)-H Bonds of α-Cyano Aliphatic Amides

被引：58

作者：

Reddy, M. Damoder ^{[1
]}

Watkins, E. Blake ^{[1
]}

机构：

[1] Union Univ, Dept Pharmaceut Sci, Sch Pharm, Jackson, TN 38305 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 22期

关键词：

C-H BONDS; STEREOSELECTIVE-SYNTHESIS; AMINO-ACIDS; ALKYLATION; FUNCTIONALIZATION; ACTIVATION; CARBONYLATION; C(SP(2))-H; REDUCTION; 8-AMINOQUINOLINE;

D O I：

10.1021/acs.joc.5b02138

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pd(OAc)(2)-catalyzed arylation of C(sp(3))-H bonds in alpha-cyano-alpha-methyl aliphatic amides is achieved in the presence of 8-aminoquinoline, as a removable directing group, using Mn(OAc)(2) and Na2CO3. The current strategy enables the placement of an aryl/heteroaryl group at the beta-position of alpha-cyano aliphatic acids for the first time. Wide functional group tolerance and easily accessible starting materials provide an efficient protocol for the synthesis of arylated alpha-cyano amides. Furthermore, the synthetic utility of the products has been demonstrated by their efficient conversions to medicinally important alpha,alpha-dialkylated acid and beta-amino acid derivatives.

引用

页码：11447 / 11459

页数：13

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