Sterically demanding Csp2(ortho-substitution)-Csp3(tertiary) bond formation via carboxylate-directed Mizoroki-Heck reaction under extra-ligand-free conditions

Wei Zeng; Ai-Wen Chen; Ming-Jie Yan; Jie Wang

doi:10.1039/d3ob01784b

Sterically demanding Csp²(ortho-substitution)-Csp³(tertiary) bond formation via carboxylate-directed Mizoroki-Heck reaction under extra-ligand-free conditions

Org Biomol Chem. 2023 Dec 20;22(1):80-84. doi: 10.1039/d3ob01784b.

Authors

Wei Zeng^{1

2}, Ai-Wen Chen^{1

2}, Ming-Jie Yan^{1

2}, Jie Wang^{1

2

3}

Affiliations

¹ School of Chinese Materia Medica, Nanjing University of Chinese Medicine, Nanjing 210023, China. jiewang@simm.ac.cn.
² State Key Laboratory of Chemical Biology, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China.
³ University of Chinese Academy of Sciences, Beijing 100049, China.

PMID: 38051230
DOI: 10.1039/d3ob01784b

Abstract

Construction of the sterically demanding Csp²(oS)-Csp³(T) bond was achieved by carrying out the Pd-catalyzed carboxylate-directed Mizoroki-Heck reaction under extra-ligand-free aqueous conditions. The cooperative role of the presence of water with the absence of phosphine ligand was proposed to accelerate the migratory insertion process considerably, delivering a broad substrate scope.