Diversification of 6‐bromo‐2‐substituted Pyridine Derivatives via Suzuki‐Miyaura Cross‐Coupling. (6th April 2018)

• Record Type: Journal Article
• Authors: Lambert, Abigail E.; Carrick, Jesse D.
• Is Part Of: Journal of heterocyclic chemistry. Volume 55:Number 5(2018)
• Page Start: 1232
• Page End: 1239
• Publication Date: 2018-04-06
• Subjects: Heterocyclic compounds -- Periodicals; 547.59
• DOI: 10.1002/jhet.3144
• Languages: English
• ISSNs: 0022-152X

Abstract

Abstract : The functionalized pyridine ring is a ubiquitous moiety in numerous research areas including materials, natural products, as well as agrochemicals and is a strategic synthon for heteroaromatic synthetic method development. Pyridinyl ligand scaffolds are also frequently incorporated into the study of metal complexes for pharmaceutical applications or separation science. Convergent access to advanced synthons is critical to experimentally defining structure activity relationships and improvement of molecular performance in the aforementioned areas. The current work describes an efficient catalyst/ligand combination for accessing 2‐acetyl‐ and 2‐procarbonyl substituted pyridines via Suzuki‐Miyaura cross‐coupling with various organotrifluoroborates. Twenty examples are described with carbonyl and procarbonyl functional groups which afford subsequent access to diversified unsymmetric ketones. Substrate scope and limitation in addition to a scale up experiment are reported. Abstract :