Direct dehydrative cross-coupling of tautomerizable heterocycles with alkynes via Pd/Cu-catalyzed phosphonium coupling

Chemical Communications

Volumn 46, Issue 8, 2010, Pages 1347-1349

  Kang, Fu An ^a   Lanter, James C ^a   Cai, Chaozhong ^a   Sui, Zhihua ^a   Murray, William V ^a  

^a JOHNSON AND JOHNSON PHARMACEUTICAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; COPPER; ISOMERASE; PALLADIUM; PHOSPHONIUM DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; HYDROGEN BOND; SYNTHESIS;

EID: 76349092927     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b917777a     Document Type: Article

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25. For tautomerizable heterocycles, the "lactam form" is generally favored over the "phenol form" in both solution and solid states. 9c Therefore, higher temperatures and stronger bases can accelerate tautomerization from the former to the latter, which can also facilitate the formation of the heterocycle-phosphonium intermediates as well as their subsequent cross-coupling reactions. The reaction conditions could be potentially further optimized by using other Pd/Cu catalysts and/or ligands under milder conditions