Dehydrative Cross-Coupling of 1-Phenylethanol Catalysed by Palladium Nanoparticles Formed in situ Under Acidic Conditions

Jason Camp, Thomas Bousfield, Jay J. Dunsford, James Adams, Joshua Britton, Michael W. Fay, Athanasios Angelis-Dimakis

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

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.
LanguageEnglish
Pages3862-3874
Number of pages13
JournalSynthesis
Volume50
Issue number19
Early online date27 Aug 2018
DOIs
Publication statusPublished - Sep 2018

Fingerprint

Palladium
Nanoparticles
Sugars
Feedstocks
Metals
Stilbenes
Catalyst deactivation
Molecular oxygen
Silicon
Dehydration
Hydroxyl Radical
Energy dispersive spectroscopy
Alcohols
Transmission electron microscopy
Detectors
Imaging techniques
Catalysts
methylphenyl carbinol

Cite this

Camp, Jason ; Bousfield, Thomas ; Dunsford, Jay J. ; Adams, James ; Britton, Joshua ; Fay, Michael W. ; Angelis-Dimakis, Athanasios. / Dehydrative Cross-Coupling of 1-Phenylethanol Catalysed by Palladium Nanoparticles Formed in situ Under Acidic Conditions. In: Synthesis. 2018 ; Vol. 50, No. 19. pp. 3862-3874.
@article{88d439d13bb348aca7d1a88d0033a608,
title = "Dehydrative Cross-Coupling of 1-Phenylethanol Catalysed by Palladium Nanoparticles Formed in situ Under Acidic Conditions",
abstract = "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.",
keywords = "Glucose, Nanoparticles, Catalysis, Dehydrative heck, Palladium, glucose, nanoparticles, catalysis, palladium, dehydrative heck",
author = "Jason Camp and Thomas Bousfield and Dunsford, {Jay J.} and James Adams and Joshua Britton and Fay, {Michael W.} and Athanasios Angelis-Dimakis",
year = "2018",
month = "9",
doi = "10.1055/s-0037-1610246",
language = "English",
volume = "50",
pages = "3862--3874",
journal = "Synthesis",
issn = "0039-7881",
publisher = "Georg Thieme Verlag",
number = "19",

}

Dehydrative Cross-Coupling of 1-Phenylethanol Catalysed by Palladium Nanoparticles Formed in situ Under Acidic Conditions. / Camp, Jason; Bousfield, Thomas; Dunsford, Jay J.; Adams, James; Britton, Joshua; Fay, Michael W.; Angelis-Dimakis, Athanasios.

In: Synthesis, Vol. 50, No. 19, 09.2018, p. 3862-3874.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Dehydrative Cross-Coupling of 1-Phenylethanol Catalysed by Palladium Nanoparticles Formed in situ Under Acidic Conditions

AU - Camp, Jason

AU - Bousfield, Thomas

AU - Dunsford, Jay J.

AU - Adams, James

AU - Britton, Joshua

AU - Fay, Michael W.

AU - Angelis-Dimakis, Athanasios

PY - 2018/9

Y1 - 2018/9

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 - Glucose

KW - Nanoparticles

KW - Catalysis

KW - Dehydrative heck

KW - Palladium

KW - glucose

KW - nanoparticles

KW - catalysis

KW - palladium

KW - dehydrative heck

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

T2 - Synthesis

JF - Synthesis

SN - 0039-7881

IS - 19

ER -