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Volumn 13, Issue 9, 2011, Pages 2310-2313

Synthesis of unsymmetrically substituted bipyridines by palladium-catalyzed direct C-H arylation of pyridine N -oxides

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EID: 79955602403     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200565u     Document Type: Article
Times cited : (86)

References (66)
  • 21
    • 0000625267 scopus 로고
    • The Bipyridines
    • Katritzky, A. R., Ed.; Academic Press: Orlando, FL, USA
    • Summers, L. A. The Bipyridines. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic Press: Orlando, FL, USA, 1984; Vol. 35, p 281.
    • (1984) Advances in Heterocyclic Chemistry , vol.35 , pp. 281
    • Summers, L.A.1
  • 28
    • 77949902067 scopus 로고    scopus 로고
    • For reviews, see refs 8 a, b. Selected recent examples
    • For reviews, see refs 8 a, b. Selected recent examples: Kim, S.-H.; Rieke, R. D. Tetrahedron 2010, 66, 3135
    • (2010) Tetrahedron , vol.66 , pp. 3135
    • Kim, S.-H.1    Rieke, R.D.2
  • 42
  • 61
    • 79955575811 scopus 로고    scopus 로고
    • The ratio of 3a to 4a in all cases is close to the expected ratio for sequential formation of 4a from 3a, taking into account that 3a has only one potential coupling site whereas 1a has two. From this it can be concluded that 1a and 3a have the same reactivity toward C-H activation and no product inhibition is taking place.
    • The ratio of 3a to 4a in all cases is close to the expected ratio for sequential formation of 4a from 3a, taking into account that 3a has only one potential coupling site whereas 1a has two. From this it can be concluded that 1a and 3a have the same reactivity toward C-H activation and no product inhibition is taking place.
  • 62
    • 0039427412 scopus 로고
    • The pyridone probably derives from nucleophilic attack of the pyridine N -oxide on the bromopyridine and subsequent rearrangement; cf.;, Depending on the conditions, the pyridone was formed as the main product (65% from pyridine N -oxide, 89% from 4- tert -butylpyridine N -oxide). For details see Supporting Information.
    • The pyridone probably derives from nucleophilic attack of the pyridine N -oxide on the bromopyridine and subsequent rearrangement; cf. Ramirez, F.; von Ostwalden, P. W. J. Am. Chem. Soc. 1959, 81, 156 Depending on the conditions, the pyridone was formed as the main product (65% from pyridine N -oxide, 89% from 4- tert -butylpyridine N -oxide). For details see Supporting Information.
    • (1959) J. Am. Chem. Soc. , vol.81 , pp. 156
    • Ramirez, F.1    Von Ostwalden, P.W.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.