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Volumn 52, Issue 11, 2013, Pages 3213-3216

Cobalt-catalyzed C4-selective direct alkylation of pyridines

Author keywords

alkylation; atom economy; catalysis; heterocyclic compounds; synthetic methods

Indexed keywords

1-ALKENES; ALKYLATION PRODUCTS; ATOM ECONOMY; DIRECT ALKYLATION; HETEROCYCLIC COMPOUND; SYNTHETIC METHODS; TURNOVER NUMBER;

EID: 84874905575     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201208666     Document Type: Article
Times cited : (136)

References (61)
  • 1
    • 0004061172 scopus 로고    scopus 로고
    • 4 th ed., Blackwell Publishing, Oxford
    • J. A. Joule, K. Mills, Heterocyclic Chemistry, 4 th ed., Blackwell Publishing, Oxford, 2000, pp. 63-120
    • (2000) Heterocyclic Chemistry , pp. 63-120
    • Joule, J.A.1    Mills, K.2
  • 7
  • 9
    • 80053899534 scopus 로고    scopus 로고
    • For a review on the CH functionalization of pyridines, see:, Y. Nakao, Synthesis 2011, 3209.
    • (2011) Synthesis , pp. 3209
    • Nakao, Y.1
  • 15
    • 80755129169 scopus 로고    scopus 로고
    • B.-T. Guan, Z. Hou, J. Am. Chem. Soc. 2011, 133, 18086, and references therein. For other examples of the C2-selective functionalization of pyridines and pyridine N-oxides through CH activation, see the reviews in Refs [1] and [5].
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 18086
    • Guan, B.-T.1    Hou, Z.2
  • 18
    • 79955594686 scopus 로고    scopus 로고
    • B.-J. Li, Z.-J. Shi, Chem. Sci. 2011, 2, 488; for a review on Ir-catalyzed regioselective borylation, see
    • (2011) Chem. Sci. , vol.2 , pp. 488
    • Li, B.-J.1    Shi, Z.-J.2
  • 41
    • 78249235410 scopus 로고    scopus 로고
    • The observed branched/linear selectivity difference between the styrene derivatives and aliphatic alkenes can be ascribed to the relative stability differences in the alkylcobalt intermediates (II in Scheme 1 vs. its linear alkylmetal counterpart). Because H/D scrambling was observed at both the α- and β-positions of styrene in Scheme 5, the hydrometallation step should be reversible, at least for styrenes. The reaction between styrenes and pyridines would proceed through the thermodynamically more stable π-conjugated benzylic-cobalt intermediate, whereas the reaction of aliphatic alkenes may proceed from the kinetically favored linear alkylcobalt intermediate. For a similar discussion, see:, Y. Nakao, N. Kashihara, K. S. Kanyiva, T. Hiyama, Angew. Chem. 2010, 122, 4553
    • (2010) Angew. Chem. , vol.122 , pp. 4553
    • Nakao, Y.1    Kashihara, N.2    Kanyiva, K.S.3    Hiyama, T.4
  • 48
    • 53549085446 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 5758; for early examples, see
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 5758
  • 53
    • 79955665182 scopus 로고    scopus 로고
    • N. Yoshikai, Synlett 2011, 1047; for a general review on Co-catalyzed cross coupling reactions, see
    • (2011) Synlett , pp. 1047
    • Yoshikai, N.1
  • 61
    • 84864870972 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2012, 51, 8251; for early examples, see the review in Ref. [24].
    • (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 8251


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.