10.1021/acs.orglett.7b03229.s001
Song-Lin Zhang
Song-Lin
Zhang
Hai-Xing Wan
Hai-Xing
Wan
Wen-Feng Bie
Wen-Feng
Bie
<i>syn</i>-Fluoro- and -Oxy-trifluoromethylation
of Arylacetylenes
American Chemical Society
2017
CsF
III
Arylacetylenes One-step
syn mode
phenylboronic acid
functionalized trifluoromethylated Z
CF 3
2017-11-18 13:48:44
Journal contribution
https://acs.figshare.com/articles/journal_contribution/_i_syn_i_-Fluoro-_and_-Oxy-trifluoromethylation_of_Arylacetylenes/5615443
One-step
concurrent fluoro-trifluoromethylation across the triple
bond of arylacetylenes in a <i>syn</i> mode is enabled by
the collaboration of (phen)Cu<sup>III</sup>(CF<sub>3</sub>)<sub>3</sub> and CsF that produces chemo-, regio-, and stereoselectively (Z)-α-fluoro-β-CF<sub>3</sub> styrenes. This method can be extended to achieve <i>syn</i>-oxy-trifluoromethylation and <i>syn</i>-aryl-trifluoromethylation
of alkynes using phenoxides, alkoxides, or phenylboronic acid in place
of CsF. It opens up new opportunities for preparing various functionalized
trifluoromethylated <i>Z</i>-alkenes and demonstrates the
potential of Cu(III)–CF<sub>3</sub> complexes in organic synthesis.