Photo-induced trifunctionalization of bromostyrenes via remote radical migration reactions of tetracoordinate boron species

Chaokun Li, Shangteng Liao, Shanglin Chen, Nan Chen, Feng Zhang, Kai Yang and Qiuling Song ()
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Chaokun Li: Fujian Province University, College of Chemistry and College of Materials Science at Fuzhou University, Fuzhou
Shangteng Liao: Fujian Province University, College of Chemistry and College of Materials Science at Fuzhou University, Fuzhou
Shanglin Chen: Fujian Province University, College of Chemistry and College of Materials Science at Fuzhou University, Fuzhou
Nan Chen: Fujian Province University, College of Chemistry and College of Materials Science at Fuzhou University, Fuzhou
Feng Zhang: Fujian Province University, College of Chemistry and College of Materials Science at Fuzhou University, Fuzhou
Kai Yang: Fujian Province University, College of Chemistry and College of Materials Science at Fuzhou University, Fuzhou
Qiuling Song: Fujian Province University, College of Chemistry and College of Materials Science at Fuzhou University, Fuzhou

Nature Communications, 2022, vol. 13, issue 1, 1-12

Abstract: Abstract Tetracoordinate boron species have emerged as radical precursors via deboronation by photo-induced single electron transfer (SET) pathway. These reactions usually produce an alkyl radical and boron-bound species, and the valuable boron species are always discarded as a by-product. Given the importance of boron species, it will be very attractive if the two parts could be incorporated into the eventual products. Herein we report a photo-catalyzed strategy in which in situ generated tetracoordinated boron species decomposed into both alkyl radicals and boron species under visible light irradiation, due to the pre-installation of a vinyl group on the aromatic ring, the newly generated alkyl radical attacks the vinyl group while leaving the boron species on ipso-position, then both radical part and boron moiety are safely incorporated into the final product. Tertiary borons, secondary borons, gem-diborons as well as 1,2-diborons, and versatile electrophiles are all well tolerated under this transformation, of note, ortho-, meta- and para-bromostyrenes all demonstrated good capabilities. The reaction portraits high atom economy, broad substrate scope, and diversified valuable products with tertiary or quaternary carbon center generated, with diborons as substrates, Csp2-B and Csp3-B are established simultaneously, which are precious synthetic building blocks in chemical synthesis.

Date: 2022
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DOI: 10.1038/s41467-022-29466-3

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