Dual Visible Light Photoredox and Gold-Catalyzed Arylative Ring Expansion

被引：373

作者：

Shu, Xing-zhong ^{[1
,2
]}

Zhang, Miao ^{[3
]}

He, Ying ^{[1
,2
,4
]}

Frei, Heinz ^{[3
]}

Toste, F. Dean ^{[1
,2
]}

机构：

[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

[2] Univ Calif Berkeley, Lawrence Berkeley Natl Lab, Chem Sci Div, Berkeley, CA 94720 USA

[3] Univ Calif Berkeley, Lawrence Berkeley Natl Lab, Phys Biosci Div, 1 Cyclotron Rd, Berkeley, CA 94720 USA

[4] Nanjing Univ, Inst Chem & BioMed Sci, Nanjing 210046, Jiangsu, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2014年 / 136卷 / 16期

关键词：

C-H ARYLATION; SEMIPINACOL REARRANGEMENT; ARYL DIAZONIUM; OXYARYLATION; TRANSITION; SALTS; PHOTOCATALYSIS; COMPLEXES; CHEMISTRY; ALKYNES;

D O I：

10.1021/ja500716j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A combination of visible light photocatalysis and gold catalysis is applied to a ring expansion-oxidative arylation reaction. The reaction provides an entry into functionalized cyclic ketones from the coupling reaction of alkenyl and allenyl cycloalkanols with aryl diazonium salts. A mechanism involving generation of an electrophilic gold(III)-aryl intermediate is proposed on the basis of mechanistic studies, including time-resolved FT-IR spectroscopy.

引用

页码：5844 / 5847

页数：4

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