title: Studies of microwave-enhanced Suzuki-Miyaura vinylation of electron-rich sterically hindered substrates utilizing potassium vinyltrifluoroborate.
abstract: The Suzuki-Miyaura cross-coupling of sterically hindered and electron-rich ortho,ortho'-substituted aryl halides with potassium vinyltrifluoroborate utilizing microwave irradiation has been conducted while adjusting solvent ratio, irradiation time, and catalyst loading to find optimal conditions. Coupling of benzyl 3,5-bis(benzyloxy)-4-bromobenzoate leads to a mixture of the desired styrene derivative, and the reduced product. 4-Bromo-1,3,5-trimethoxybenzene, methyl 4-bromo-3,5-dimethoxybenzoate, and mesitylene bromide were also coupled to test the breadth and scope of this methodology. Of these substrates tested only 4-bromo-1,3,5-trimethoxybenzene was not vinylated successfully, which is believed to be due to the electron rich nature of this system.
authors.affiliation: Department of Chemistry, Trident Technical College, 7000 Rivers Ave. Charleston, SC 29455, USA.
authors.forename: Matthew D
authors.initials: MD
authors.lastname: Brooker
authors.forename: Stefan M
authors.initials: SM
authors.lastname: Cooper
authors.forename: Dena R
authors.initials: DR
authors.lastname: Hodges
authors.forename: Rhiannon R
authors.initials: RR
authors.lastname: Carter
authors.forename: Justin K
authors.initials: JK
authors.lastname: Wyatt