Selective Functionalization of sp3 C-H Bonds Adjacent to Nitrogen Using (Diacetoxyiodo)benzene (DIB)

被引：201

作者：

Shu, Xing-Zhong ^{[1
]}

Xia, Xiao-Feng ^{[1
]}

Yang, Yan-Fang ^{[1
]}

Ji, Ke-Gong ^{[1
]}

Liu, Xue-Yuan ^{[1
]}

Liang, Yong-Min ^{[1
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 19期

关键词：

RUTHENIUM-CATALYZED OXIDATION; OLEFIN CIS-DIHYDROXYLATION; TERTIARY-AMINES; MOLECULAR-OXYGEN; HYDROGEN-PEROXIDE; ELECTROORGANIC CHEMISTRY; ANODIC-OXIDATION; BETA-LACTAMS; ACTIVATION; EPOXIDATION;

D O I：

10.1021/jo901583r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A PhI(OAc)(2) mediated selective functionalization of sp(3) C-H bonds adjacent to a nitrogen atom has been reported. When piperidine derivates were used, direct diacetoxylation of alpha and beta sp(3) C-H adjacent to a nitrogen atom were observed to afford various cis-2,3-diacetoxylated piperidines. On the other hand, tetrahydroisoquinoline derivatives gave various alpha-C-H functionalized products in the presence of PhI(OAc)(2). Nitroalkanes, dialkyl malonates, and beta-keto ester are active participants in this coupling reaction. Meanwhile, alpha-amino nitriles can also be obtained by oxidative coupling of amines with malononitrile.

引用

页码：7464 / 7469

页数：6

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