Palladium-Catalyzed Borylation of Aryl Chlorides: Scope, Applications, and Computational Studies

From chloride to boronate: Catalysts comprising palladium and biaryl monophosphine ligands provide highly active systems for the borylation of aryl and heteroaryl chlorides (see scheme). Symmetrical and unsymmetrical biaryl products can also be prepared directly from two aryl chlorides without isola...

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Published inAngewandte Chemie (International ed.) Vol. 46; no. 28; pp. 5359 - 5363
Main Authors Billingsley, Kelvin L, Barder, Timothy E, Buchwald, Stephen L
Format Journal Article
LanguageEnglish
Published Weinheim Wiley-VCH Verlag 01.01.2007
WILEY-VCH Verlag
WILEY‐VCH Verlag
Wiley
Subjects
boronate esters
borylation
Catalysis
Chemistry
Chemistry, Multidisciplinary
Chlorides - chemistry
Computers
CC coupling
Kinetics
Ligands
Models, Molecular
Molecular Structure
palladium
Palladium - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
Suzuki-Miyaura coupling
Temperature
Thermodynamics
C-C coupling
ORGANOBORON COMPOUNDS
HALIDES
SYSTEM
CROSS-COUPLING REACTION
ONE-POT SYNTHESIS
borylation
COMPLEXES
Suzuki-Miyaura coupling
DENSITY
boronate esters
palladium
INSIGHTS
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Summary:From chloride to boronate: Catalysts comprising palladium and biaryl monophosphine ligands provide highly active systems for the borylation of aryl and heteroaryl chlorides (see scheme). Symmetrical and unsymmetrical biaryl products can also be prepared directly from two aryl chlorides without isolation of the intermediate boronate esters. Computational studies provide insight into the roles of the biaryl phosphine ligand and the KOAc base in the catalytic cycle.
Bibliography:http://dx.doi.org/10.1002/anie.200701551
ark:/67375/WNG-BRC0PH60-B
National Institutes of Health - No. GM 46059
NSF - No. CHE 9808061; No. DBI 9729592
Amgen
Boehringer Ingelheim
We thank the National Institutes of Health (GM 46059) for support of this work. We are grateful to Merck, Amgen, Boehringer Ingelheim, BASF (Pd(OAc)2), and Saltigo (XPhos) for additional support. The Varian NMR instruments used in this work were purchased with funding from the NSF (CHE 9808061 and DBI 9729592).
istex:174713C225F61D6F2BBC271B1CF4F07F144FCCD3
Merck
ArticleID:ANIE200701551
and Saltigo (XPhos) for additional support. The Varian NMR instruments used in this work were purchased with funding from the NSF (CHE 9808061 and DBI 9729592).
2
We thank the National Institutes of Health (GM 46059) for support of this work. We are grateful to Merck, Amgen, Boehringer Ingelheim, BASF (Pd(OAc)
Medline
NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200701551