TY - JOUR
T1 - Dehydrative Cross-Coupling of 1-Phenylethanol Catalysed by Palladium Nanoparticles Formed in situ Under Acidic Conditions.
AU - Camp, Jason E.
AU - Bousfield, Thomas W.
AU - Dunsford, Jay J.
AU - Adams, James
AU - Britton, Joshua
AU - Fay, Michael W.
AU - Angelis-Dimakis, Athanasios.
N1 - M1 - Copyright (C) 2018 American Chemical Society (ACS). All Rights Reserved.
CAPLUS AN 2018:1604774(Journal; Online Computer File)
PY - 2018/8/27
Y1 - 2018/8/27
N2 - A dehydrative cross-coupling of 1-phenylethanol catalysed by sugar derived, in situ formed palladium(0) nanoparticles under acidic conditions is realised. The acidic conditions allow for use of alcohols as a feedstock in metal-mediated coupling reactions via their in situ dehydration and subsequent cross-coupling. Extensive analysis of the size and morphology of the palladium nanoparticles formed in situ showed that the zero-valent metal was surrounded by hydrophilic hydroxyl groups. EDX-TEM imaging studies using a prototype silicon drift detector provided insight into the problematic role of molecular oxygen in the system. This increased understanding of the catalyst deactivation allowed for the development of the cross-coupling methodology. A 250-12,000 fold increase in molar efficiency was observed when compared to related two-step protocols that use alternative feedstocks for the palladium-mediated synthesis of stilbenes. This work opens up a new research area in which the active catalyst is formed, stabilised and regenerated by a renewable sugar.
AB - A dehydrative cross-coupling of 1-phenylethanol catalysed by sugar derived, in situ formed palladium(0) nanoparticles under acidic conditions is realised. The acidic conditions allow for use of alcohols as a feedstock in metal-mediated coupling reactions via their in situ dehydration and subsequent cross-coupling. Extensive analysis of the size and morphology of the palladium nanoparticles formed in situ showed that the zero-valent metal was surrounded by hydrophilic hydroxyl groups. EDX-TEM imaging studies using a prototype silicon drift detector provided insight into the problematic role of molecular oxygen in the system. This increased understanding of the catalyst deactivation allowed for the development of the cross-coupling methodology. A 250-12,000 fold increase in molar efficiency was observed when compared to related two-step protocols that use alternative feedstocks for the palladium-mediated synthesis of stilbenes. This work opens up a new research area in which the active catalyst is formed, stabilised and regenerated by a renewable sugar.
KW - stilbene aryl alkene prepn regioselective
KW - phenylethanol stilbene aryl iodide Mizoroki Heck coupling palladium catalyst
UR - http://www.scopus.com/inward/record.url?scp=85053683751&partnerID=8YFLogxK
U2 - 10.1055/s-0037-1610246
DO - 10.1055/s-0037-1610246
M3 - Article
VL - 50
SP - 3862
EP - 3874
JO - Synthesis
JF - Synthesis
SN - 0039-7881
IS - 19
ER -
