A Ba/Pd Catalytic System Enables Dehydrative Cross-Coupling and Excellent E-Selective Wittig Reactions

Peizhong Xie; Weishan Fu; Xinying Cai; Zuolian Sun; Ying Wu; Shuangshuang Li; Cuiqing Gao; Xiaobo Yang; Teck-Peng Loh

doi:10.1021/acs.orglett.9b02623

A Ba/Pd Catalytic System Enables Dehydrative Cross-Coupling and Excellent E-Selective Wittig Reactions

Org Lett. 2019 Sep 6;21(17):7055-7059. doi: 10.1021/acs.orglett.9b02623. Epub 2019 Aug 20.

Authors

Peizhong Xie¹, Weishan Fu¹, Xinying Cai¹, Zuolian Sun¹, Ying Wu¹, Shuangshuang Li¹, Cuiqing Gao², Xiaobo Yang¹, Teck-Peng Loh^{1

3}

Affiliations

¹ School of Chemistry and Molecular Engineering, Institute of Advanced Synthesis, Nanjing Tech University, Nanjing 211816, P. R. China.
² Co-Innovation Center for the Sustainable Forestry in Southern China, College of Forestry, Nanjing Forestry University, Nanjing 210037, China.
³ Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371.

PMID: 31430163
DOI: 10.1021/acs.orglett.9b02623

Abstract

A Ba/Pd cooperative catalysis system was developed to enable the dehydrative cross-coupling of allylic alcohols with P-ylides to occur directly and promote a subsequent Wittig reaction in one pot. A variety of multisubstituted 1,4-dienes were isolated in good to excellent yields with broad P-ylides (stabilized by both ester and ketone carbonyl groups) and aldehyde (aliphatic and aromatic) substrates with excellent E selectivity.