Department of Chemistry, Princeton University, Princeton, New Jersey 08544, United States
J. Am. Chem. Soc., Article ASAP
DOI: 10.1021/jacs.6b03215
Publication Date (Web): May 10, 2016
Copyright © 2016 American Chemical Society
Abstract
We report here the remarkable properties of PAd3, a crystalline air-stable solid accessible through a scalable SN1 reaction. Spectroscopic data reveal that PAd3,
benefiting from the polarizability inherent to large hydrocarbyl
groups, exhibits unexpected electron releasing character that exceeds
other alkylphosphines and falls within a range dominated by
N-heterocyclic carbenes. Dramatic effects in catalysis are also enabled
by PAd3 during Suzuki–Miyaura cross-coupling of
chloro(hetero)arenes (40 examples) at low Pd loading, including the
late-stage functionalization of commercial drugs. Exceptional space-time
yields are demonstrated for the syntheses of industrial precursors to
valsartan and boscalid from chloroarenes with ∼2 × 104 turnovers in 10 min.
benefiting from the polarizability inherent to large hydrocarbyl
groups, exhibits unexpected electron releasing character that exceeds
other alkylphosphines and falls within a range dominated by
N-heterocyclic carbenes. Dramatic effects in catalysis are also enabled
by PAd3 during Suzuki–Miyaura cross-coupling of
chloro(hetero)arenes (40 examples) at low Pd loading, including the
late-stage functionalization of commercial drugs. Exceptional space-time
yields are demonstrated for the syntheses of industrial precursors to
valsartan and boscalid from chloroarenes with ∼2 × 104 turnovers in 10 min.
0 件のコメント:
コメントを投稿