Pd-Catalyzed TBHP-Mediated Selective Wacker-Type Oxidation and Oxo-acyloxylation of Olefins Using a 2-(1H-Indazol-1-yl)quinoline Ligand

Shuaizhong Zhang, Jinquan Zhang and Hongbin Zou*

*College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, P. R. China, Email: zouhbzju.edu.cn

S. Zhang, J. Zhang, H. Zou, Org. Lett., 2023, 25, 1850-1855.

DOI: 10.1021/acs.orglett.3c00326

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Abstract

A Pd(II)-catalyzed selective oxidation of olefins using tert-butyl hydroperoxide as the oxidant and 2-(1H-indazol-1-yl)quinoline as the ligand provides methyl ketones, whereas the presence of Ac₂O initiated an oxo-acyloxylation to afford α-acetoxyacetone products.

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proposed mechanism

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Key Words

Wacker Oxidation, TBHP

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ID: J54-Y2023