The Selective Nickel‐Catalyzed N‐Allylation of C3‐Unprotected Indoles under Mild and Clean Conditions. Issue 26 (1st March 2022)

• Record Type: Journal Article
• Authors: Mouhsine, Bouchaib; Karim, Abdallah; Dumont, Clément; Saint Pol, Anthony; Suisse, Isabelle; Sauthier, Mathieu
• Is Part Of: European journal of organic chemistry. Volume 2022:Issue 26(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-03-01
• Subjects: Allyl alcohol -- Dimethylsulfoxide -- Indole -- N-allylation -- Nickel; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202200042
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A simple salt free and selective N ‐allylation of indoles with allylic alcohols has been developed. The protocol uses a catalytic amount of a nickel complex generated in situ from Ni(cod)2 and dppf as diphosphine. The use of DMSO as the reaction solvent is crucial to control the regioselectivity of the reaction with the exclusive formation of the N ‐allyl product among up to three possible products. Abstract : Indoles are selectively N‐allylated according to a salt‐free nickel catalyzed reaction with allylic alcohols as co‐reagents. The use of DMSO as the reaction solvent is crucial to control the regioselectivity of the reaction with the exclusive formation of the N‐allyl product among up to three possible products.