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Photo-induced trifunctionalization of bromostyrenes via remote radical migration reactions of tetracoordinate boron species.
- Source :
- Nature Communications; 4/4/2022, Vol. 13 Issue 1, p1-12, 12p
- Publication Year :
- 2022
-
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, Csp<superscript>2</superscript>-B and Csp<superscript>3</superscript>-B are established simultaneously, which are precious synthetic building blocks in chemical synthesis. Tetracoordinate boron species are common radical precursors in organic synthesis, but the boron species are discarded as by-products. Herein the authors report a strategy to incorporate both the alkyl moiety and boron species into the eventual products, yielding organoboron compounds. [ABSTRACT FROM AUTHOR]
- Subjects :
- BORON
VINYL polymers
ALKYL radicals
ORGANOBORON compounds
CHARGE exchange
Subjects
Details
- Language :
- English
- ISSN :
- 20411723
- Volume :
- 13
- Issue :
- 1
- Database :
- Complementary Index
- Journal :
- Nature Communications
- Publication Type :
- Academic Journal
- Accession number :
- 156102425
- Full Text :
- https://doi.org/10.1038/s41467-022-29466-3