Asymmetric Intermolecular Heck Reaction of Aryl Halides

Chunlin Wu and Jianrong Zhou (Steve)*

*Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371, Email: jrzhountu.edu.sg

C. Wu, J. Zhou, J. Am. Chem. Soc., 2014, 136, 650-652.

DOI: 10.1021/ja412277z

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Abstract

In an asymmetric intermolecular Heck reaction, various cyclic olefins coupled with aryl and vinyl bromides in high enantioselectivity. Only bisphosphine oxides on a spiro backbone formed highly stereoselective Pd catalysts. The use of alkylammonium salts and alcoholic solvents were essential to promote halide dissociation from the arylpalladium intermediate.

see article for more examples

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Palladium-Catalyzed, Asymmetric Mizoroki-Heck Reaction of Benzylic Electrophiles Using Phosphoramidites as Chiral Ligands

Z. Yang, J. Zhou, J. Am. Chem. Soc., 2012, 134, 11833-11835.

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Key Words

Heck reaction, 2,5-dihydrofurans, cyclopentenes, 3-pyrrolines

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ID: J48-Y2014