Hiyama Cross-Coupling of Arenediazonium Salts under Mild Reaction Conditions

被引：56

作者：

Cheng, Kai ^{[1
,2
,4
]}

Wang, Chen ^{[1
,2
]}

Ding, Yiyuan ^{[3
]}

Song, Qingbao ^{[3
]}

Qi, Chenze ^{[1
,2
]}

Zhang, Xian-Man ^{[1
,2
]}

机构：

[1] Univ Shaoxing, Inst Appl Chem, Shaoxing 312000, Zhejiang, Peoples R China

[2] Univ Shaoxing, Dept Chem, Shaoxing 312000, Zhejiang, Peoples R China

[3] Zhejiang Univ Technol, Coll Chem & Mat Sci, Hangzhou 310014, Zhejiang, Peoples R China

[4] Zhejiang Huangma Chem Ind Grp Co Ltd, Shangyu 312363, Zhejiang, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 22期

关键词：

TRIETHYLAMMONIUM BIS(CATECHOL) SILICATES; ACTIVE PALLADIUM CATALYSTS; REDUCTION-CYCLIZATION HRC; SUZUKI-MIYAURA REACTION; HECK-TYPE ARYLATION; ARYL BROMIDES; ROOM-TEMPERATURE; DIAZONIUM SALTS; BOND-FORMATION; ARYLDIAZONIUM TETRAFLUOROBORATE;

D O I：

10.1021/jo201437j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Palladium acetate [Pd(OAc)(2)]-catalyzed Hiyama cross-coupling of arenediazonium salts with organosilanes was found to generate biaryl products in high yields in alcoholic solutions. The simple and efficient protocol does not require any bases, ligands, or air/moisture. The transformation can tolerate either electron-donating or electron-withdrawing functional groups. Theoretical studies show that the transmetalation is the rate-limiting step for the cross-coupling reaction and both acetate and tetrafluoroborate anions may be involved in the direct reaction with the silicon atom.

引用

页码：9261 / 9268

页数：8

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