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
› Institutsangaben
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.
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Publikationsverlauf

Received: 30. November 2019

Accepted after revision: 17. Dezember 2019

Publikationsdatum:
10. Februar 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