Highly E‐Selective Olefin Synthesis Catalysed by Novel Quinoxalinone Photocatalyst under Visible Light Conditions

In photo‐induced olefin synthesis, the photocatalysts with high triplet energy could cause the isomerization of olefins. This study demonstrates a new quinoxalinone photocatalytic system for highly stereoselective alkenes preparation from alkenyl sulfones and alkyl boronic acids. Our photocatalyst c...

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Bibliographic Details
Published in:Chemistry : a European journal 2023-05, Vol.29 (27), p.e202300360-n/a
Main Authors: Xu, Xin, Huang, Jie, Gao, Dandan, Wang, Jiahua, Tang, Xiang‐Ying, Wang, Long
Format: Article
Language:English
Subjects:
Acids
Alkenes
Alkynes
boronic acids
Chemical synthesis
Chemistry
E-selective olefins
Isomerization
NMR
Nuclear magnetic resonance
Oxidation
Photocatalysis
Photocatalysts
quinoxalinone
Stereoselectivity
Sulfones
two-in-one
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Summary:In photo‐induced olefin synthesis, the photocatalysts with high triplet energy could cause the isomerization of olefins. This study demonstrates a new quinoxalinone photocatalytic system for highly stereoselective alkenes preparation from alkenyl sulfones and alkyl boronic acids. Our photocatalyst could not convert the thermodynamically favored E‐olefin to Z‐olefin, guaranteeing the high E‐configuration selectivity of the reaction. There is weak interaction between boronic acids and quinoxalinone according to NMR experiments, probably decreasing the oxidation potential of boronic acids. This system can be further extended to the allyl and alkynyl sulfones to give corresponding alkenes and alkynes. An efficient method for the synthesis of highly E‐selective olefins directly utilizing alkyl boronic acids as radical precursors was developed, catalysed by novel quinoxalinone‐type catalyst.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.202300360