Divergent Access to (1, 1) and (1, 2)‐Azidolactones from Alkenes using Hypervalent Iodine Reagents. Issue 40 (27th June 2017)

• Record Type: Journal Article
• Authors: Alazet, Sébastien; Le Vaillant, Franck; Nicolai, Stefano; Courant, Thibaut; Waser, Jerome
• Is Part Of: Chemistry. Volume 23:Issue 40(2017)
• Page Start: 9501
• Page End: 9504
• Publication Date: 2017-06-27
• Subjects: 1, 2 shift -- azides -- hypervalent iodine -- lactones -- photoredox; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201702599
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: 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. Abstract : From one to two : A versatile synthesis of azidolactones from alkenes and carboxylic acids has been developed based on photoredox and palladium catalysis. (1, 1) and (1, 2)‐azido lactones can be selectively synthesized through the choice of benziodoxole reagent and catalyst. These transformations have been carried out under mild conditions using low catalyst loadings and give access to a large scope of azidolactones.