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Volumn 15, Issue 24, 2009, Pages 5950-5955

Heteroaromatic tosylates as electrophiles in regioselective Mizoroki-Heck-coupling reactions with electron-rich olefins

Author keywords

Aryl tosylates; C C coupling; Heterocycles; Mizoroki Heck coupling; Palladium

Indexed keywords

ARYL TOSYLATES; BENZYLIC AMIDES; C-C COUPLING; CATALYTIC SYSTEM; COUPLING REACTION; ELECTRON-RICH OLEFINS; ELECTROPHILES; FUNCTIONALIZED; HECK COUPLING; HETEROAROMATIC COMPOUNDS; HETEROCYCLES; LARGE-SCALE APPLICATIONS; MESYLATES; MIZOROKI-HECK COUPLING; PYRIDYL; REGIO-SELECTIVE; SYNTHETIC UTILITY;

EID: 66349100984     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200900313     Document Type: Article
Times cited : (54)

References (57)
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    • For references on heteroaromatic MH-coupling reactions with halide electrophiles: Ref. [5c, 6b]; a)T. J. Kwok, J. A. Virgilio, Org. Process Res. Dev. 2005, 9, 694-696.
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    • Djakovitch and co-workers reported a 30% conversion in the MH coupling of 8-quinolinyl mesylate to acrolein. To our knowledge this is the only reported example of a non-fluorinated sulfonate as an electrophile in an MH coupling, see: S. Noël, C. Pinel, L. Djakovitch, Org. Biomol. Chem. 2006, 4, 3760-3762.
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    • In solution, the 2-hydroxy pyridines are in equilibrium with their tautomeric pyridinone species. In some cases, this resulted in mixtures of isomeric tosylates which however were separable by column chromatography, see: F.-A. Kang, Z. Sui, W. V. Murray, Eur. J. Org. Chem. 2009, 461-479, and references therein.
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    • No reaction was observed with the similar O,O-diphenyl-or O,O-diethyl 2-pyridyl phosphates with full recovery of the starting materials.
    • No reaction was observed with the similar O,O-diphenyl-or O,O-diethyl 2-pyridyl phosphates with full recovery of the starting materials.
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    • See the Supporting Information for precise experimental details in the scale-up study
    • See the Supporting Information for precise experimental details in the scale-up study.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.