Nickel-Catalyzed Cross-Coupling of Allyl Alcohols with Aryl- or Alkenylzinc Reagents

Bo Yang; Zhong-Xia Wang

doi:10.1021/acs.joc.6b02564

Nickel-Catalyzed Cross-Coupling of Allyl Alcohols with Aryl- or Alkenylzinc Reagents

J Org Chem. 2017 May 5;82(9):4542-4549. doi: 10.1021/acs.joc.6b02564. Epub 2016 Nov 17.

Authors

Bo Yang¹, Zhong-Xia Wang^{1

2}

Affiliations

¹ CAS Key Laboratory of Soft Matter Chemistry and Department of Chemistry, University of Science and Technology of China , Hefei, Anhui 230026, P. R. China.
² Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) , Tianjin 300072, P. R. China.

PMID: 28472890
DOI: 10.1021/acs.joc.6b02564

Abstract

Nickel-catalyzed cross-coupling of allyl alcohols with aryl- and alkenylzinc chlorides through C-O bond cleavage was performed. Reaction of (E)-3-phenylprop-2-en-1-ol and 1-aryl-prop-2-en-1-ols with aryl- or alkenylzinc chlorides gave linear cross-coupling products. Reaction of 1-phenyl- or 1-methyl-substituted (E)-3-phenylprop-2-en-1-ol with aryl- or alkenylzinc chlorides resulted in 3-aryl/alkenyl-substituted (E)-(prop-1-ene-1,3-diyl)dibenzenes or 3-aryl/alkenyl-substituted (E)-(but-1-enyl)benzene. Reaction of allyl alcohol with p-Me₂NC₆H₄ZnCl resulted in a mixture of normal coupling product 4-allyl-N,N-dimethylaniline and its isomerized product N,N-dimethyl-4-(prop-1-en-1-yl)aniline.

Publication types

Research Support, Non-U.S. Gov't