Hydroboration Catalyzed by 1,2,4,3-Triazaphospholenes

被引：38

作者：

Tien, Chieh-Hung ^{[1
]}

Adams, Matt R. ^{[1
]}

Ferguson, Michael J. ^{[2
]}

Johnson, Erin R. ^{[1
]}

Speed, Alexander W. H. ^{[1
]}

机构：

[1] Dalhousie Univ, Dept Chem, 6274 Coburg Rd,POB 15000, Halifax, NS B3H 4R2, Canada

[2] Univ Alberta, Dept Chem, Xray Crystallog Lab, Edmonton, AB T6G 2G2, Canada

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 20期

基金：

加拿大自然科学与工程研究理事会;

关键词：

STABLE CARBENE; DERIVATIVES; REDUCTION; BORANE; 1,3,4-TRIPHENYL-4,5-DIHYDRO-1H-1,2,4-TRIAZOL-5-YLIDENE; HYDROGENATION; PRECURSORS; REACTIVITY; SALTS; BASE;

D O I：

10.1021/acs.orglett.7b02695

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis and study of the catalytic activity of 1,2,4,3-triazaphospholenes (TAPs) is reported. TAPs represent a more modular scaffold than previously reported diazaphospholenes. TAP halides were shown to catalyze the 1,2 hydroboration of 19 imines, and three alpha,beta unsaturated aldehydes with pinacolborane, including examples that did not undergo hydroboration by previously reported diazaphospholene systems. DFT calculations support a mechanism where a triazaphospholene cation interacts with the substrate, a mechanism distinct from diazaphospholene catalyzed hydroborations.

引用

页码：5565 / 5568

页数：4

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