Iridium-Catalyzed Distal Hydroboration of Aliphatic Internal Alkenes

Guangzhu Wang; Xinyi Liang; Lili Chen; Qian Gao; Jian-Guo Wang; Panke Zhang; Qian Peng; Senmiao Xu

doi:10.1002/anie.201902464

Iridium-Catalyzed Distal Hydroboration of Aliphatic Internal Alkenes

Angew Chem Int Ed Engl. 2019 Jun 11;58(24):8187-8191. doi: 10.1002/anie.201902464. Epub 2019 May 8.

Authors

Guangzhu Wang^{1

2}, Xinyi Liang³, Lili Chen², Qian Gao², Jian-Guo Wang³, Panke Zhang¹, Qian Peng³, Senmiao Xu²

Affiliations

¹ College of Chemistry and Molecular Engineering, Henan Institute of Advanced Technology, Zhengzhou University, Zhengzhou, 450001, China.
² State Key Laboratory for Oxo Synthesis and Selective Oxidation, Center for Excellence in Molecular Synthesis, Suzhou Research Institute, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, 730000, China.
³ State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, 300071, China.

PMID: 30990948
DOI: 10.1002/anie.201902464

Abstract

The regioselective hydroboration of aliphatic internal alkenes remains a great challenge. Reported herein is an iridium-catalyzed hydroboration of aliphatic internal alkenes, providing distal-borylated products in good to excellent yields with high regioselectivity (up to 99:1). We also demonstrate that the C-B bond of the distal-borylated product can be readily converted into other functional groups. DFT calculations indicate that the reaction proceeds through an unexpected Ir^III /Ir^V cycle.

Keywords: alkenes; alkyl boronic acids; hydroboration; iridium; synthetic methods.

Abstract

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