Bifunctional Ligand Enables Efficient Gold-Catalyzed Hydroalkenylation of Propargylic Alcohol

被引：33

作者：

Liao, Shengrong ^{[1
,2
]}

Porta, Alessio ^{[3
]}

Cheng, Xinpeng ^{[2
]}

Ma, Xu ^{[2
]}

Zanoni, Giuseppe ^{[3
]}

Zhang, Liming ^{[2
]}

机构：

[1] Chinese Acad Sci, Key Lab Trop Marine Bioresources & Ecol, South China Sea Inst Oceanol, Guangzhou, Guangdong, Peoples R China

[2] UCSB, Dept Chem & Biochem, Santa Barbara, CA 93106 USA

[3] Univ Pavia, Dept Chem, Viale Taramelli,10, I-27100 Pavia, Italy

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 27期

关键词：

conjugation; gold; ligand design; reaction mechanisms; synthetic methods; DIELS-ALDER REACTION; ARYLBORONIC ACIDS; ORGANOBORONIC ACIDS; ALKYNES; CYCLOISOMERIZATIONS; REGIOSELECTIVITY; ISOMERIZATIONS; HYDROARYLATION; ACTIVATION; ALDEHYDES;

D O I：

10.1002/anie.201802533

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Using the previously designed biphenyl-2-ylphosphine ligand, featuring a remote tertiary amino group, the first gold-catalyzed intermolecular hydroalkenylation of alkynes has been developed. Synthetically valuable conjugated dienyl alcohols are formed in moderate to good yields. A range of alkenyltrifluoroborates are allowed as the alkenyl donor, and no erosion of alkene geometry and/or the propargylic configuration are detected. DFT calculations confirm the critical role of the remote basic group in the ligand as a general-base catalyst for promoting this novel gold catalysis with good efficiency.

引用

页码：8250 / 8254

页数：5

共 63 条

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