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

Liang-Jun Xie; Lili Chen; Senmiao Xu

doi:10.1055/a-2335-8677

Synthesis, Inhaltsverzeichnis

Synthesis 2024; 56(17): 2638-2647
DOI: 10.1055/a-2335-8677

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

Liang-Jun Xie

^aState Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, P. R. of China

^bUniversity of Chinese Academy of Sciences, Beijing 100049, P. R. of China

,

Lili Chen∗

^aState Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, P. R. of China

^cState 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 ∗

^aState Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, P. R. of China

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Abstract

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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.

Key words

asymmetric catalysis - borylation - chiral bidentate boryl ligands - C–H activation - synthetic methods

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