Diversification of 6-bromo-2-substituted Pyridine Derivatives via Suzuki-Miyaura Cross-Coupling

被引:7
作者
Lambert, Abigail E. [1 ]
Carrick, Jesse D. [1 ]
机构
[1] Tennessee Technol Univ, Dept Chem, 55 Univ Dr, Cookeville, TN 38505 USA
基金
美国国家科学基金会;
关键词
ANTITUMOR-ACTIVITY; GENERAL-SOLUTION; IRON CHELATORS; CAERULOMYCIN-C; BORONIC ACIDS; COMPLEXES; ARYL; HETEROARYL; CHLORIDES; LIGANDS;
D O I
10.1002/jhet.3144
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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 toa scale up experiment are reported.
引用
收藏
页码:1232 / 1239
页数:8
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