Copper-Catalyzed Borylative Methylation of Alkyl Iodides with CO as the C1 Source: Advantaged by Faster Reaction of CuH over CuBpin

Fu-Peng Wu; Xiao-Feng Wu

doi:10.1002/anie.202102197

Copper-Catalyzed Borylative Methylation of Alkyl Iodides with CO as the C1 Source: Advantaged by Faster Reaction of CuH over CuBpin

Angew Chem Int Ed Engl. 2021 May 17;60(21):11730-11734. doi: 10.1002/anie.202102197. Epub 2021 Apr 16.

Authors

Fu-Peng Wu^{1

2}, Xiao-Feng Wu^{1

2}

Affiliations

¹ Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Straße 29a, 18059, Rostock, Germany.
² Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 116023, Dalian, Liaoning, China.

PMID: 33694252
DOI: 10.1002/anie.202102197

Abstract

CuH and CuBpin are versatile catalysts and intermediates in organic chemistry. However, studies that involve both CuH and CuBpin in the same reaction is still rarely reported due to their high reactivity. Now, a study on CuH- and CuBpin-catalyzed borylative methylation of alkyl iodides with CO as the C1 source is reported. Various one carbon prolongated alkyl boranes (RCH₂ Bpin and RCH(Bpin)₂ ) were produced in moderate to good yields from the corresponding alkyl iodides (RI). In this cooperative system, CuH reacts with alkyl iodide faster than CuBpin.

Keywords: alkyl iodides; borylmethylation; carbonylation; copper boryl; copper hydride.

Grants and funding

China Scholarship Council