Synlett
DOI: 10.1055/s-0036-1588572
cluster
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Decarboxylation of Benzyl Fluorobenzoates

Yusuke Makida, Yasutaka Matsumoto, Ryoichi Kuwano*
  • Department of Chemistry, Faculty of Science, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395, Japan   Email: rkuwano@chem.kyushu-univ.jp
This work was supported by Grant-in-Aid for Young Scientists (B) (JSPS KAKENHI Grant Number JP17K14450).
Further Information

Publication History

Received: 19 June 2017

Accepted after revision: 28 August 2017

Publication Date:
26 September 2017 (eFirst)

Published as part of the Cluster CO Activation

Abstract

The decarboxylation of benzyl fluorobenzoates has been developed by using the palladium catalyst prepared in situ from Pd(η3-allyl)Cp and bulky monophosphine ligand XPhos. The catalytic reaction afforded a range of fluorinated diarylmethanes in good yields with broad functional-group compatibility. The substrates were readily synthesized by condensation of the corresponding benzoic acid with benzyl alcohol. Therefore, the transformation is formally regarded as a cross-coupling reaction between fluorine-containing benzoic acids and benzyl alcohols.

Supporting Information