85267-92-1Relevant articles and documents
Copper-catalyzed cyanomethylation of allylic alcohols with concomitant 1,2-aryl migration: Efficient synthesis of functionalized ketones containing an α-quaternary center
Bunescu, Ala,WangDr, Qian,Zhu, Jieping
, p. 3132 - 3135 (2015)
A copper-catalyzed alkylation of allylic alcohols by alkyl nitriles with concomitant 1,2-aryl migration was developed. Formation of the alkyl nitrile radical was followed by its intermolecular addition to alkenes and the migration of a vicinal aryl group with the concomitant generation of a carbonyl functionality to complete the domino sequence. Mechanistic studies suggested that 1,2-aryl migration proceeded through a radical pathway (neophyl rearrangement). The protocol provided an efficient route to functionalized ketones containing an α-quaternary center.