Practical and convenient synthesis of 1,6-di- or 1,2,5,6-tetra-arylhexa-1,3,5-trienes by the dimerization of Pd(0)-complexed alkenylcarbenes generated from π-allylpalladium intermediates

Yoshikazu Horino; Yu Takahashi; Kaori Koketsu; Hitoshi Abe; Kiyoshi Tsuge

doi:10.1021/ol501643x

Practical and convenient synthesis of 1,6-di- or 1,2,5,6-tetra-arylhexa-1,3,5-trienes by the dimerization of Pd(0)-complexed alkenylcarbenes generated from π-allylpalladium intermediates

Org Lett. 2014 Jun 20;16(12):3184-7. doi: 10.1021/ol501643x. Epub 2014 Jun 12.

Authors

Yoshikazu Horino¹, Yu Takahashi, Kaori Koketsu, Hitoshi Abe, Kiyoshi Tsuge

Affiliation

¹ Department of Applied Chemistry and ‡Department of Chemistry, Graduate School of Science and Engineering, University of Toyama , Gofuku, Toyama 930-855, Japan.

PMID: 24921935
DOI: 10.1021/ol501643x

Abstract

Pd(0)-complexed 3-aryl or 2,3-diaryl propenylcarbenes generated from α-silyl-, α-germyl-, or α-boryl-σ-allylpalladium intermediates undergo self-dimerization to provide 1,6-di- or 1,2,5,6-tetraarylhexa-1,3,5-trienes in good to high yields. This method allows the use of a π-allylpalladium intermediate for a carbenoid precursor. Furthermore, the obtained 1,2,5,6-tetraarylhexa-1,3,5-trienes exhibit aggregation-induced emission enhancement property.