title: Direct stereoselective α-arylation of unmodified enals using an organocatalytic cross-coupling-like reaction.
abstract: Cross-coupling reactions typically rely on the use of transition metal catalysis. However, although achieving this process using metal-free organocatalysts is highly challenging, it could offer unique opportunities to discover novel bond-forming strategies in organic synthesis. Here we report a new amine catalysed direct stereoselective C-H α-arylation reaction of unmodified enals with bromoarenes. The power of this process, which involves an unprecedented iminium-Michael-alkylation-enamine-retro-Michael cascade sequence, has been demonstrated in the context of direct α-functionalization reactions of simple, unmodified enals with 4-bromophenols, 1-bromo-2-naphthol and 3-bromoindoles under mild reaction conditions. Notably, the process can be used for highly stereoselective syntheses of non-readily accessible E isomers, which normally require the use of transition metal-promoted cross-couplings and functionalized enals. The results of these studies significantly expand the scope of aminocatalysis.
authors: Department of Chemistry & Chemical Biology, University of New Mexico, Albuquerque, New Mexico 87131-0001, USA.
authors: Xixi
authors: X
authors: Song
authors: Aiguo
authors: A
authors: Song
authors: Fang
authors: F
authors: Zhang
authors: He-Xing
authors: HX
authors: Li
authors: Wei
authors: W
authors: Wang
mesh_terms: D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D007211:Indoles / Q000737:chemistry; D015394:Molecular Structure; D009284:Naphthols / Q000737:chemistry; D010636:Phenols / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D007211:Indoles; D009284:Naphthols; D010636:Phenols; C028405:2-naphthol