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- Title
Dehydrogenative Synthesis of 2,2′‐Bipyridyls through Regioselective Pyridine Dimerization.
- Authors
Yamada, Shuya; Kaneda, Takeshi; Steib, Philip; Murakami, Kei; Itami, Kenichiro
- Abstract
2,2′‐Bipyridyls have been utilized as indispensable ligands in metal‐catalyzed reactions. The most streamlined approach for the synthesis of 2,2′‐bipyridyls is the dehydrogenative dimerization of unfunctionalized pyridine. Herein, we report on the palladium‐catalyzed dehydrogenative synthesis of 2,2′‐bipyridyl derivatives. The Pd catalysis effectively works with an AgI salt as the oxidant in the presence of pivalic acid. A variety of pyridines regioselectively react at the C2‐positions. This dimerization method is applicable for challenging substrates such as sterically hindered 3‐substituted pyridines, where the pyridines regioselectively react at the C2‐position. This reaction enables the concise synthesis of twisted 3,3′‐disubstituted‐2,2′‐bipyridyls as an underdeveloped class of ligands.
- Subjects
DEHYDROGENATION; REGIOSELECTIVITY (Chemistry); PYRIDINE synthesis; DIMERIZATION; LIGANDS (Chemistry); METAL catalysts
- Publication
Angewandte Chemie, 2019, Vol 131, Issue 25, p8429
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201814701