C-C Bond-Forming Strategy by Manganese-Catalyzed Oxidative Ring-Opening Cyanation and Ethynylation of Cyclobutanol Derivatives

被引：187

作者：

Ren, Rongguo ^{[1
]}

Wu, Zhen ^{[1
]}

Xu, Yan ^{[1
]}

Zhu, Chen ^{[1
,2
]}

机构：

[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, 199 Ren Ai Rd, Suzhou 215123, Jiangsu, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synth Chem Nat Subst, 345 Lingling Rd, Shanghai 200032, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 08期

基金：

中国国家自然科学基金;

关键词：

alkynylation; cyanation; cyclobutanol; manganese catalysis; ring-opening; TERT-CYCLOBUTANOLS; H FLUORINATION; ASYMMETRIC ARYLATION; C(SP(3))-H BONDS; VINYL AZIDES; CLEAVAGE; CYCLOPROPANOLS; ALKYNYLATION; KETONES; EFFICIENT;

D O I：

10.1002/anie.201510973

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel C-C bond-forming strategy employing manganese-catalyzed ring-opening of cyclobutanol substrates, followed by cyanation or ethynylation, is described. A cyano C1 unit and ethynyl C2 unit are regiospecifically introduced to the g-position of ketones at room temperature, providing a mild yet powerful method for production of elusive aliphatic nitriles and alkynes. All transformations described are based on a common sequence: 1) oxidative ring-opening of cyclobutanol substrates by C-C bond cleavage; 2) radical addition to triple bonds bearing an arylsulfonyl group; and 3) radical-mediated C-S bond cleavage.

引用

页码：2866 / 2869

页数：4

共 67 条

[1]

[Anonymous], 2015, ANGEW CHEM INT EDIT

[2]

[Anonymous], 2015, ANGEW CHEM, V127, P424, DOI DOI 10.1038/NBT896

[3] THE INVENTION OF RADICAL REACTIONS .23. NEW REACTIONS - NITRILE AND THIOCYANATE TRANSFER TO CARBON RADICALS FROM SULFONYL CYANIDES AND SULFONYL ISOTHIOCYANATES [J].