Boraformylation and Silaformylation of Allenes

Tetsuaki Fujihara; Ayumi Sawada; Tatsuya Yamaguchi; Yosuke Tani; Jun Terao; Yasushi Tsuji

doi:10.1002/anie.201611314

Boraformylation and Silaformylation of Allenes

Angew Chem Int Ed Engl. 2017 Feb 1;56(6):1539-1543. doi: 10.1002/anie.201611314. Epub 2017 Jan 11.

Authors

Tetsuaki Fujihara¹, Ayumi Sawada¹, Tatsuya Yamaguchi¹, Yosuke Tani^{1

2}, Jun Terao^{1

3}, Yasushi Tsuji¹

Affiliations

¹ Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Kyoto, 615-8510, Japan.
² Present address: Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka, 560-0043, Japan.
³ Present address: Department of Basic Science, Graduate School of Art and Sciences, The University of Tokyo, Tokyo, 153-8902, Japan.

PMID: 28074601
DOI: 10.1002/anie.201611314

Abstract

The boraformylation of allenes with B₂ (pin)₂ and a formate ester as boron and formyl source, respectively, proceeds in the presence of a copper catalyst. The reaction selectively affords the corresponding β-boryl β,γ-unsaturated aldehydes in good to high yields. Furthermore, the silaformylation of allenes was achieved with a formate ester and PhMe₂ Si-B(pin) as the silicon source.

Keywords: allenes; borylation; copper; formate esters; silylation.

Publication types

Research Support, Non-U.S. Gov't