Premium
Divergent Access to (1,1) and (1,2)‐Azidolactones from Alkenes using Hypervalent Iodine Reagents
Author(s) -
Alazet Sébastien,
Le Vaillant Franck,
Nicolai Stefano,
Courant Thibaut,
Waser Jerome
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201702599
Subject(s) - hypervalent molecule , reagent , catalysis , chemistry , azide , lewis acids and bases , combinatorial chemistry , iodine , organic chemistry , sodium azide , photoredox catalysis , radical , photocatalysis
A versatile synthesis of azidolactones through azidation and cyclization of carboxylic acids onto alkenes has been developed. Based on either photoredox or palladium catalysis, (1,1) and (1,2) azido lactones can be selectively synthesized. The choice of catalyst and benziodoxol(on)e reagent serving as azide source was essential to initiate either a radical or Lewis acid mediated process with divergent outcome. These transformations were carried out under mild conditions using a low catalyst loading and gave access to a large scope of azido lactones.