Palladacycle-Catalyzed Carbonylative Suzuki–Miyaura Coupling with High Turnover Number and Turnover Frequency

This work reports the carbonylative Suzuki–Miyaura coupling of aryl iodides catalyzed by palladacycles. More importantly, the palladacycles have been used to generate high turnover numbers (TON’s) and turnover frequencies (TOF’s). A range of aryl iodides can be coupled with arylboronic acids, genera...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 80; no. 15; pp. 7810 - 7815
Main Authors Gautam, Prashant, Bhanage, Bhalchandra M
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.08.2015
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
TRIARYLPHOSPHITE COMPLEXES
C-C
HETEROARYL HALIDES
ARYL IODIDES
AMINOCARBONYLATION
EFFICIENT
BROMIDES
ARYLBORONIC ACIDS
PALLADIUM CATALYSTS
BIARYL KETONES
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Summary:This work reports the carbonylative Suzuki–Miyaura coupling of aryl iodides catalyzed by palladacycles. More importantly, the palladacycles have been used to generate high turnover numbers (TON’s) and turnover frequencies (TOF’s). A range of aryl iodides can be coupled with arylboronic acids, generating TON’s in the range of 106 to 107 and TOF’s in the range of 105 to 106 h–1. Comparison of the palladacycles with a conventional palladium source shows their superiority in generating high TON’s and TOF’s.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b01160