Synthesis
DOI: 10.1055/a-2335-8677
feature

Benzothiazole-Directed Enantioselective Borylation of Secondary Benzylic C–H Bonds Using Iridium Catalysis

Liang-Jun Xie
a   State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, P. R. of China
b   University of Chinese Academy of Sciences, Beijing 100049, P. R. of China
,
Lili Chen
a   State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, P. R. of China
c   State Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, P. R. of China
,
Senmiao Xu
a   State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, P. R. of China
› Author Affiliations
The authors thank the National Key Research and Development Program of China (2022YFA1504302), the National Natural Science Foundation of China (92256302 and 22331011), the Natural Science Foundation of Jiangsu Province (BK20211092), and the Major Program of the Lanzhou Institute of Chemical Physics, CAS (No. ZYFZFX-9) for funding.


Abstract

Reported here is the iridium-catalyzed regio- and enantio­selective secondary benzylic C–H borylation using benzothiazole as the directing group. Various monosubstituted 2-arylalkylbenzo[d]thiazole were well-tolerated, affording the corresponding products in moderate to good yields with good enantioselectivity. The C–B bond in one boryl­ated product could undergo stereospecific transformations to form a series of C–C and C–heteroatom bonds.

Supporting Information



Publication History

Received: 26 April 2024

Accepted after revision: 29 May 2024

Accepted Manuscript online:
29 May 2024

Article published online:
24 June 2024

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