Issue 47, 2022

Probing B–X to B–H conversions and applications in C–F bond activation catalysis

Abstract

Herein we exploit a catalytic amount of [Ph3C]+ to initiate B–X to B–H bond conversion with Et3SiH. This was applied to 6 haloboranes. However, 9-X-9-borabicyclo[3.3.1]nonane (B-X-9-BBN, X = F, Br) reacts directly with silane. Thus, C–F bond activation of benzyl fluorides in the presence of arenes afforded the Friedel–Crafts (FC) products using B–H-9-BBN in the presence of Et3SiH. This catalysis was probed with a range of arenes and several benzyl fluoride derivatives. The protocol is simple, cheap and a convenient route to 1,1-diarylmethanes from benzyl fluorides in good to excellent yields (up to 99%) under mild conditions.

Graphical abstract: Probing B–X to B–H conversions and applications in C–F bond activation catalysis

Supplementary files

Article information

Article type
Communication
Submitted
07 Huk 2022
Accepted
24 Huk 2022
First published
24 Huk 2022

Dalton Trans., 2022,51, 17962-17966

Probing B–X to B–H conversions and applications in C–F bond activation catalysis

A. Yeganeh-Salman, I. Elser, K. L. Bamford, D. Ebanks and D. W. Stephan, Dalton Trans., 2022, 51, 17962 DOI: 10.1039/D2DT03588J

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