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![Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F51444.jpg&w=3840&q=50)
Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions
Published on: March 20, 2014
Reductive Cross-Coupling of Alkynes with Aryl Bromides via Zr/Pd Synergistic Catalysis
Marymoud Erzuah1, Abhishek Raj1, Rebecca A Kehner1
1Department of Chemistry and Biochemistry, Baylor University, Waco, Texas 76706, United States.
Abstract:
The cocatalytic reductive cross-coupling of unactivated alkynes with aryl bromides is reported, using 2 mol % Pd(PPh3)4 and 10 mol % Cp2ZrCl2 in combination with a hydrosilane reductant. Hydroarylated products are furnished in upward of 91% yield across 25 elaborated substrates, including those containing unprotected alcohols, esters, amides, and terminal alkenes. Syn-selective hydrozirconation of alkyne substrates prior to transmetalation ensures exceptional (>20:1) (E)-selectivity across all alkene products. Further, this protocol was successfully implemented on gram scale without loss of efficiency or selectivity.
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