Premium
Photochemical Strain‐Release‐Driven Cyclobutylation of C(sp 3 )‐Centered Radicals
Author(s) -
Ernouf Guillaume,
Chirkin Egor,
Rhyman Lydia,
Ramasami Ponnadurai,
Cintrat JeanChristophe
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201908951
Subject(s) - cyclobutanes , radical , bicyclic molecule , chemistry , reactivity (psychology) , butane , olefin fiber , photoredox catalysis , photolyase , photochemistry , catalysis , medicinal chemistry , stereochemistry , organic chemistry , cycloaddition , photocatalysis , medicine , pathology , alternative medicine , biochemistry , dna repair , gene
A new photoredox‐catalyzed decarboxylative radical addition approach to functionalized cyclobutanes is described. The reaction involves an unprecedented formal Giese‐type addition of C(sp 3 )‐centered radicals to highly strained bicyclo[1.1.0]butanes. The mild photoredox conditions, which make use of a readily available and bench stable phenyl sulfonyl bicyclo[1.1.0]butane, proved to be amenable to a diverse range of α‐amino and α‐oxy carboxylic acids, providing a concise route to 1,3‐disubstituted cyclobutanes. Furthermore, kinetic studies and DFT calculations unveiled mechanistic details on bicyclo[1.1.0]butane reactivity relative to the corresponding olefin system.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom