title: A General Palladium-Catalyzed Hiyama Cross-Coupling Reaction of Aryl and Heteroaryl Chlorides.
abstract: A general palladium-catalyzed Hiyama cross-coupling reaction of aryl and heteroaryl chlorides with aryl and heteroaryl trialkoxysilanes by a Pd(OAc)2 /L2 catalytic system is presented. A newly developed water addition protocol can dramatically improve the product yields. The conjugation of the Pd/L2 system and the water addition protocol can efficiently catalyze a broad range of electron-rich, -neutral, -deficient, and sterically hindered aryl chlorides and heteroaryl chlorides with excellent yields within three hours and the catalyst loading can be down to 0.05 mol % Pd for the first time. Hiyama coupling of heteroaryl chlorides with heteroaryl silanes is also reported for the first time. The reaction can be easily scaled up 200 times (100 mmol) without any degasification and purification of reactants; this facilitates the practical application in routine synthesis.
authors.affiliation: State Key Laboratory of Chirosciences and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong, P. R. of China.|The Hong Kong Polytechnic University Shenzhen Research Institute (SZRI), Shenzhen, P. R. of China.
authors.forename: On Ying
authors.initials: OY
authors.lastname: Yuen
authors.affiliation: State Key Laboratory of Chirosciences and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong, P. R. of China. bccmso@polyu.edu.hk.|The Hong Kong Polytechnic University Shenzhen Research Institute (SZRI), Shenzhen, P. R. of China. bccmso@polyu.edu.hk.
authors.forename: Chau Ming
authors.identifier: http://orcid.org/0000-0001-6268-651X
authors.initials: CM
authors.lastname: So
authors.affiliation: State Key Laboratory of Chirosciences and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong, P. R. of China.
authors.forename: Ho Wing
authors.initials: HW
authors.lastname: Man
authors.affiliation: State Key Laboratory of Chirosciences and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong, P. R. of China. fuk-yee.kwong@polyu.edu.hk.|The Hong Kong Polytechnic University Shenzhen Research Institute (SZRI), Shenzhen, P. R. of China. fuk-yee.kwong@polyu.edu.hk.
authors.forename: Fuk Yee
authors.identifier: http://orcid.org/0000-0001-9105-1740
authors.initials: FY
authors.lastname: Kwong
keywords: aryl chlorides; aryl(alkoxy)silane; cross-coupling reaction; palladium; phosphine ligand