In:
Nature Communications, Springer Science and Business Media LLC, Vol. 13, No. 1 ( 2022-04-04)
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, C sp 2 -B and C sp 3 -B are established simultaneously, which are precious synthetic building blocks in chemical synthesis.
Type of Medium:
Online Resource
ISSN:
2041-1723
DOI:
10.1038/s41467-022-29466-3
Language:
English
Publisher:
Springer Science and Business Media LLC
Publication Date:
2022
detail.hit.zdb_id:
2553671-0
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