title: Regiocontrolled synthesis of (hetero)aryl and alkenyl dehydropyrrolidines, dehydropiperidines and azepenes by Ru-catalyzed, heteroatom-directed α-C-H activation/cross-coupling of cyclic enamides with boronic acids.
abstract: The synthesis of α-aryl and alkenyl pyrrolidine-, piperidine-, and azepane derivatives, through the intermediacy of cyclic enamides is described. The desired outcome is achieved through ruthenium-catalyzed, site-selective sp(2) C-H activation/cross-coupling with aryl and alkenyl boronic acids. The regioselectivity (α-sp(2)vs. α-sp(3)vs. β-sp(2) C-H functionalization) is governed by the rate differences between sp(2) and sp(3) C-H activation and the necessity for chelation between the ruthenium metal and the carbonyl directing group.
authors.affiliation: Department of Chemistry, Central Washington University, Ellensburg, WA 98926, USA. TimothyB@cwu.edu.
authors.forename: Timothy K
authors.initials: TK
authors.lastname: Beng
authors.forename: Spencer
authors.initials: S
authors.lastname: Langevin
authors.forename: Hannah
authors.initials: H
authors.lastname: Braunstein
authors.forename: Monique
authors.initials: M
authors.lastname: Khim