Rhodium-Catalyzed C-H/C-H Cross Coupling of Benzylthioethers or Benzylamines with Thiophenes Enabled by Flexible Directing Groups

被引：21

作者：

Yang, Shiping ^{[1
]}

Cheng, Rui ^{[1
]}

Zhao, Tingxing ^{[1
]}

Luo, Anping ^{[1
]}

Lan, Jingbo ^{[1
]}

You, Jingsong ^{[1
]}

机构：

[1] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, 29 Wangjiang Rd, Chengdu 610064, Sichuan, Peoples R China

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 13期

关键词：

CARBOXYLIC-ACIDS; ARYLATION; BOND; THIOETHERS; LIGAND; OLEFINATION; ACCESS;

D O I：

10.1021/acs.orglett.9b01679

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reported herein is an efficient synthetic protocol to ortho-functionalized 2-aryl thiophenes via Rh(III)-catalyzed C-H/C-H cross coupling of benzylthioethers or benzylamines with thiophenes. Both ortho- and meta-substituted benzylthioethers give monoheteroarylated products, while ortho-unhindered substrates mainly provide diheteroarylated benzylthioethers. The C-H/C-H cross coupling of benzylamines with thiophenes exclusively generates diheteroarylated benzaldehydes. Mechanistic investigation discloses a three-step tandem process involving the ortho-C-H diheteroarylation of benzylamine, the oxidation of benzylamine to imine, and the hydrolysis of imine to aldehyde.

引用

页码：5086 / 5090

页数：5

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