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Boronic Acid Mediated Carbocyanation of Olefins and Vinylation of Alkyl Iodides
Author(s) -
Hara Reina,
Khiar Chahinaz,
Dange Nitin S.,
Bouillac Pierre,
Robert Frédéric,
Landais Yannick
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800444
Subject(s) - chemistry , alkyl , iodide , aryl , boronic acid , phenylboronic acid , iodine , organic chemistry , steric effects , carbon atom , catalysis , medicinal chemistry
Phenylboronic acid was shown to mediate the multicomponent free‐radical carbocyanation of olefins and the addition of alkyl iodides to vinylsulfones. The reaction of the boronic acid with di‐ tert ‐butyl hyponitrite generates an aryl radical, which can selectively abstract an iodine atom from an alkyl iodide to form the key carbon‐centered radical precursor. Arylboronic acids are thus considered efficient tin surrogates in this free‐radical process.