Synthesis 2020; 52(09): 1407-1416
DOI: 10.1055/s-0039-1691564
paper
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed ortho-Monoacylation of Arenes with Aldehydes­ via 1,2,4-Benzotriazine-Directed C–H Bond Activation

Jin Liu
a   Hubei Key Laboratory of Kidney Disease Pathogenesis and Intervention, School of Medicine, Hubei Polytechnic University, Huangshi 435003, P. R. of China   Email: cbc_hbpu@163.com
d   Huangshi Shi Xing Pharmaceutical Co., Ltd., Huangshi 435003, P. R. of China
,
Shaofen Jin
c   Graduate School, Hubei Normal University, Huangshi 435003, P. R. of China
,
Yingxing Zhou
a   Hubei Key Laboratory of Kidney Disease Pathogenesis and Intervention, School of Medicine, Hubei Polytechnic University, Huangshi 435003, P. R. of China   Email: cbc_hbpu@163.com
,
Dongmei Ni
a   Hubei Key Laboratory of Kidney Disease Pathogenesis and Intervention, School of Medicine, Hubei Polytechnic University, Huangshi 435003, P. R. of China   Email: cbc_hbpu@163.com
,
Tingting Liu
a   Hubei Key Laboratory of Kidney Disease Pathogenesis and Intervention, School of Medicine, Hubei Polytechnic University, Huangshi 435003, P. R. of China   Email: cbc_hbpu@163.com
,
Bingcun Cui
a   Hubei Key Laboratory of Kidney Disease Pathogenesis and Intervention, School of Medicine, Hubei Polytechnic University, Huangshi 435003, P. R. of China   Email: cbc_hbpu@163.com
,
Gang Hu
a   Hubei Key Laboratory of Kidney Disease Pathogenesis and Intervention, School of Medicine, Hubei Polytechnic University, Huangshi 435003, P. R. of China   Email: cbc_hbpu@163.com
,
Xin Yu
a   Hubei Key Laboratory of Kidney Disease Pathogenesis and Intervention, School of Medicine, Hubei Polytechnic University, Huangshi 435003, P. R. of China   Email: cbc_hbpu@163.com
,
Guosheng Huang
b   State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. of China   Email: hgs2368@163.com
› Author Affiliations
We thank the State Key Laboratory of Applied Organic Chemistry, Talent Introduction Project of Hubei Polytechnic University (No.19XJK03R), and Medical School (HBPU) for financial support.
Further Information

Publication History

Received: 30 November 2019

Accepted after revision: 17 December 2019

Publication Date:
10 February 2020 (online)


Abstract

An efficient palladium-catalyzed C–H bond functionalization/ortho-monoacylation reaction of 3-aryl-1,2,4-benzotriazines with (hetero)aryl or alkyl aldehydes has been developed, which offers a facile and alternative strategy for direct modification and further diversification of 3-aryl-1,2,4-benzotriazines. Bioactive 1,2,4-benzotriazine has been employed as a novel directing group for the palladium-catalyzed regioselective monoacylation of sp2 C–H bond protocol with broad substrate scope and good functional group tolerance.

Supporting Information