Issue 10, 2015

Successive Cu/Pd transmetalation relay catalysis in stereoselective synthesis of tetraarylethenes

Abstract

A new and efficient strategy for the synthesis of tetraaryl-substituted olefins has been developed. With a Cu/Pd-catalyzed isomerization/insertion/oxidative coupling cascade reaction of cyclopropene with internal alkynes, a wide variety of cis-tetrasubstituted olefins were synthesized in good yields as single stereoisomers. The photophysical properties of these novel tetraarylethenes were fully characterized and proved to be good AIE (aggregation-induced emission) luminogens. Experimental studies and theoretical calculation indicated that Cu(I) and Pd(II) were the actual catalysts. A novel deprotonative Cu-catalyzed cyclopropene cycloisomerization and subsequent successive Cu/Pd transmetalation relay mechanism was proposed for the discovered reaction.

Graphical abstract: Successive Cu/Pd transmetalation relay catalysis in stereoselective synthesis of tetraarylethenes

Supplementary files

Article information

Article type
Research Article
Submitted
30 Jun 2015
Accepted
05 Aug 2015
First published
06 Aug 2015

Org. Chem. Front., 2015,2, 1366-1373

Author version available

Successive Cu/Pd transmetalation relay catalysis in stereoselective synthesis of tetraarylethenes

C. Song, Y. Sun, J. Wang, H. Chen, J. Yao, C. Tung and Z. Xu, Org. Chem. Front., 2015, 2, 1366 DOI: 10.1039/C5QO00205B

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