NDLI: Photoinitiated carbonyl-metathesis: deoxygenative reductive olefination of aromatic aldehydes via photoredox catalysis† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c9sc00711c

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Photoinitiated carbonyl-metathesis: deoxygenative reductive olefination of aromatic aldehydes via photoredox catalysis† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c9sc00711c

Content Provider	Semantic Scholar
Author	Wang, Shun Lokesh, N. Hioe, Johnny Gschwind, Ruth M. König, Burkhard
Copyright Year	2019
Abstract	Carbonyl-carbonyl olefination, known as McMurry reaction, represents a powerful strategy for the construction of olefins. However, catalytic variants that directly couple two carbonyl groups in a single reaction are less explored. Here, we report a photoredox-catalysis that uses B2pin2 as terminal reductant and oxygen trap allowing for deoxygenative olefination of aromatic aldehydes under mild conditions. This strategy provides access to a diverse range of symmetrical and unsymmetrical alkenes with moderate to high yield (up to 83%) and functional-group tolerance. To follow the reaction pathway, a series of experiments were conducted including radical inhibition, deuterium labelling, fluorescence quenching and cyclic voltammetry. Furthermore, NMR studies and DFT calculations were combined to detect and analyze three active intermediates: a cyclic three-membered anionic species, an α-oxyboryl carbanion and a 1,1-benzyldiboronate ester. Based on these results, we propose a mechanism for the C[double bond, length as m-dash]C bond generation involving a sequential radical borylation, "bora-Brook" rearrangement, B2pin2-mediated deoxygenation and a boron-Wittig process.
Starting Page	4580
Ending Page	4587
Page Count	8
File Format	PDF HTM / HTML
DOI	10.1039/c9sc00711c
PubMed reference number	31123568
Journal	Medline
Volume Number	10
Alternate Webpage(s)	https://pubs.rsc.org/en/content/articlepdf/2019/sc/c9sc00711c
Alternate Webpage(s)	https://pubs.rsc.org/en/content/articlepdf/2019/sc/c9sc00711c?page=search
Alternate Webpage(s)	https://epub.uni-regensburg.de/38446/4/c9sc00711c.pdf
Alternate Webpage(s)	http://www.rsc.org/suppdata/c9/sc/c9sc00711c/c9sc00711c1.pdf
Alternate Webpage(s)	https://doi.org/10.1039/c9sc00711c
Journal	Chemical science
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article

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