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Facet‐Dependent Catalytic Activity of Palladium Nanocrystals in Tsuji–Trost Allylic Amination Reactions with Product Selectivity
Author(s) -
Chanda Kaushik,
Rej Sourav,
Liu ShuYa,
Huang Michael H.
Publication year - 2015
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201500300
Subject(s) - amination , selectivity , octahedron , catalysis , allylic rearrangement , chemistry , coupling reaction , aniline , palladium , organic chemistry , crystal structure
Pd nanocubes, cuboctahedra, and octahedra with good size control were used to catalyze CN bond formation in the Tsuji–Trost allylic amination reaction of aniline. Nanocubes gave either monoallylaniline or diallylaniline depending on the amount of allyl bromide used, but the octahedra and cuboctahedra only gave mixtures of monoallylaniline and diallylaniline under the same reaction conditions. The Pd nanocubes were stable over multiple cycles of the reaction. The cubes and octahedra were demonstrated to catalyze the amination reaction by using a wide variety of substituted anilines, but the cubes were the best catalyst with consistently the highest efficiency, product yield, and product selectivity. This work demonstrates that the use of metal nanocrystals with proper facet control is important for catalyzing coupling reactions with product selectivity.