Boraformylation and Silaformylation of Allenes. Issue 6 (11th January 2017)

• Record Type: Journal Article
• Authors: Fujihara, Tetsuaki; Sawada, Ayumi; Yamaguchi, Tatsuya; Tani, Yosuke; Terao, Jun; Tsuji, Yasushi
• Is Part Of: Angewandte Chemie international edition. Volume 56:Issue 6(2017)
• Page Start: 1539
• Page End: 1543
• Publication Date: 2017-01-11
• Subjects: allenes -- borylation -- copper -- formate esters -- silylation; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201611314
• Languages: English
• ISSNs: 1433-7851

Abstract

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. Abstract : Boron or silicon? Boraformylation and silaformylation reactions of allenes with formate esters smoothly proceed in the presence of a copper catalyst using B2 (pin)2 and PhMe2 Si−B(pin) as the boron and silicon source, respectively. These reactions selectively afford the corresponding β‐boryl and β‐silyl β, γ‐unsaturated aldehydes in good to high yields with excellent regioselectivity.