Iridium-Catalyzed Regio- and Enantioselective Borylation of Unbiased Methylene C(sp3 )-H Bonds at the Position β to a Nitrogen Center

Rongrong Du; Luhua Liu; Senmiao Xu

doi:10.1002/anie.202016009

Iridium-Catalyzed Regio- and Enantioselective Borylation of Unbiased Methylene C(sp³ )-H Bonds at the Position β to a Nitrogen Center

Angew Chem Int Ed Engl. 2021 Mar 8;60(11):5843-5847. doi: 10.1002/anie.202016009. Epub 2021 Jan 29.

Authors

Rongrong Du^{1

2}, Luhua Liu^{1

2}, Senmiao Xu^{1

3}

Affiliations

¹ 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.
² University of Chinese Academy of Sciences, Beijing, 100049, China.
³ Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou, 311121, China.

PMID: 33325578
DOI: 10.1002/anie.202016009

Abstract

Reported herein is the pyrazole-directed iridium-catalyzed enantioselective borylation of unbiased methylene C-H bonds at the position β to a nitrogen center. The combination of a chiral bidentate boryl ligand, iridium precursor, and pyrazole directing group was responsible for the high regio- and enantioselectivity observed. The method tolerated a vast array of functional groups to afford the corresponding C(sp³ )-H functionalization products with good to excellent enantioselectivity.

Keywords: C−H borylation; asymmetric catalysis; chiral amines; organoboron compounds; pyrazoles.

Abstract

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