Ni-Catalyzed Suzuki-Miyaura Cross-Coupling of α-Oxo-vinylsulfones To Prepare C-Aryl Glycals and Acyclic Vinyl Ethers

被引：90

作者：

Gong, Liang ^{[1
,2
,3
]}

Sun, Hong-Bao ^{[1
,2
,3
]}

Deng, Li-Fan ^{[1
,2
,3
]}

Zhang, Xia ^{[1
,2
,3
]}

Liu, Jie ^{[1
,2
,3
]}

Yang, Shengyong ^{[1
,2
,3
]}

Niu, Dawen ^{[1
,2
,3
]}

机构：

[1] Sichuan Univ, West China Hosp, State Key Lab Biotherapy, Dept Emergency, Chengdu 610041, Sichuan, Peoples R China

[2] Sichuan Univ, West China Hosp, Ctr Canc, Chengdu 610041, Sichuan, Peoples R China

[3] Sichuan Univ, Sch Chem Engn, Chengdu 610041, Sichuan, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2019年 / 141卷 / 19期

关键词：

BORONIC ACIDS; ARYLBORONIC ACIDS; BOND-CLEAVAGE; STEREOSELECTIVE-SYNTHESIS; TRANSITION-METALS; GRIGNARD-REAGENTS; CARBON-SULFUR; ACTIVATION; ELECTROPHILES; SULFONES;

D O I：

10.1021/jacs.9b02312

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We demonstrate that readily available and bench-stable alpha-oxo-vinylsulfones are competent electrophiles in Ni-catalyzed Suzuki-Miyaura cross-coupling reactions. The C-sulfone bond in the alpha-oxo-vinylsulfone motif is cleaved chemoselectively in these reactions, furnishing C-aryl glycals or acyclic vinyl ethers in high yields. These reactions proceed under mild conditions and tolerate a remarkable scope of heterocycles and functional groups. Preliminary mechanistic studies revealed the importance of an alpha-heteroatom in facilitating these transformations.

引用

页码：7680 / 7686

页数：7

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