title: Synthesis of 3-substituted isoindolin-1-ones via a tandem desilylation, cross-coupling, hydroamidation sequence under aqueous phase-transfer conditions.
abstract: A simple and expedient method for the synthesis of 3-methylene-isoindolin-1-ones 4 under aqueous phase-transfer conditions has been developed. Starting from 2-iodobenzamides 1 and (silyl)alkynes, the products are obtained in high yields and short reaction times (30 min) with the use of inexpensive CuCl/PPh3 catalyst system in the presence of n-Bu4NBr (TBAB) as a phase-transfer agent. Terminal alkynes are conveniently "unmasked" upon in situ desilylation under the reaction conditions. Alkynes possessing heterocyclic moieties were also found as amenable substrates. Furthermore, a one-pot process starting from 2-iodobenzamides 1, aryl halides (bromides or iodides) and trimethylsilylacetylene (TMSA) as a convenient acetylene surrogate was also shown to be feasible under Pd/Cu catalysis.
authors.affiliation: Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, University Park, Los Angeles, CA-90089-1661, USA. gprakash@usc.edu.
authors.forename: Socrates B
authors.initials: SB
authors.lastname: Munoz
authors.forename: Alexandra N
authors.initials: AN
authors.lastname: Aloia
authors.forename: Alexander K
authors.initials: AK
authors.lastname: Moore
authors.forename: Attila
authors.initials: A
authors.lastname: Papp
authors.forename: Thomas
authors.initials: T
authors.lastname: Mathew
authors.forename: Santos
authors.initials: S
authors.lastname: Fustero
authors.forename: George A
authors.initials: GA
authors.lastname: Olah
authors.forename: G K Surya
authors.initials: GK
authors.lastname: Prakash