Leveraging the Hydroarylation of α-(Trifluoromethyl)styrenes to Access Trifluoromethylated All-Carbon Quaternary Centers

被引：18

作者：

Vayer, Marie ^{[1
]}

Mayer, Robert J. ^{[1
]}

Moran, Joseph ^{[2
]}

Leboeuf, David ^{[1
]}

机构：

[1] Univ Strasbourg, F-67000 Strasbourg, France

[2] Univ Strasbourg, France Inst Univ France IUF, F-75005 Strasbourg, Paris, France

来源：

ACS CATALYSIS | 2022年 / 12卷 / 17期

关键词：

alpha-(trifluoromethyl)styrenes; hydroarylation; hexafluoroisopropanol; Bronsted acid; all-carbon quaternary centers; HIGHLY ENANTIOSELECTIVE CONSTRUCTION; GEM-DIFLUOROALKENES; CONJUGATE ADDITION; BOND ACTIVATION; H BOND; STEREOCENTERS; EFFICIENT; FLUORINE; LEWIS; HEXAFLUOROISOPROPANOL;

D O I：

10.1021/acscatal.2c03330

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

alpha-(Trifluoromethyl)styrenes are attractive olefin building blocks that have eluded hydroarylation processes. Here, we demonstrate that the use of a promoter system featuring triflic acid and hexafluoroisopropanol enables hydroarylation to directly build trifluoromethylated all-carbon quaternary centers. The observed reactivity significantly enriches the scope of hydroarylation of unactivated styrenes and provides straightforward access to trifluoromethylated diarylalkanes of interest. Gram-scale reactions and further functionalizations illustrate the synthetic potential of this approach.

引用

页码：10995 / 11001

页数：7

共 85 条

[1]

Ackermann L, 2018, CATALYTIC HYDROARYLATION OF CARBON-CARBON MULTIPLE BONDS, P1

[2] Carbon Trifluoromethylation Reactions of Hydrocarbon Derivatives and Heteroarenes [J].