Photoredox-Catalyzed Hydrocarboxymethylation of Alkenes

被引：14

作者：

Fang, Jie ^{[1
,2
]}

Hu, Qiang ^{[1
]}

Dong, Wan-Li ^{[1
]}

Xu, Guo-Qiang ^{[1
]}

Hu, Xiu-Qin ^{[1
]}

Luo, Yong-Chun ^{[1
]}

Xu, Peng-Fei ^{[1
]}

机构：

[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

[2] Jiangxi Acad Sci, Inst Appl Chem, Nanchang 330096, Jiangxi, Peoples R China

来源：

CCS CHEMISTRY | 2021年 / 3卷 / 10期

关键词：

photoredox catalysis; unactivated alkenes; bromoacetic acid; two-carbon synthon; fatty acids; TRANSFER RADICAL-ADDITION; ALPHA; ALPHA-DIFLUOROARYLACETIC ACIDS; UNACTIVATED ALKENES; CARBON-DIOXIDE; DECARBOXYLATIVE ALKYNYLATION; HYDROTRIFLUOROMETHYLATION; CARBOXYLATION; DIFLUOROMETHYLATION; ACCESS;

D O I：

10.31635/ccschem.020.202000542

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Direct introduction of a carboxyl group into molecules is one of the most useful methods for the preparation of carboxylic acids, which avoids the conversion of various preexisting functional groups and features good step- and atom-economy. However, the methods for the direct synthesis of two-carbon added carboxylic acids from the precursors remain rare. Herein, we first report a general and mild method for the direct synthesis of a range of aliphatic acids by photoredox-catalyzed hydrocarboxymethylation of alkenes with good toleration of various functional groups in which bromoacetic acid is utilized as an ideal two-carbon synthon. The synthetic utility of this hydrocarboxymethylation protocol is further demonstrated by the concise synthesis of two marketed drugs, sensipar and tirofiban, from commercially available starting materials. [GRAPHICS] .

引用

页码：95 / 104

页数：10

共 64 条

[1]

[Anonymous], 2017, Visible Light Photocatalysis in Organic Chemistry

[2] Photo-Organocatalysis of Atom-Transfer Radical Additions to Alkenes [J].