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Volumn 13, Issue 9, 2011, Pages 2228-2231

NHC-catalyzed oxidative cyclization reactions of 2-alkynylbenzaldehydes under aerobic conditions: Synthesis of O-Heterocycles

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; BENZALDEHYDE DERIVATIVE; FUSED HETEROCYCLIC RINGS;

EID: 79955607386     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200481u     Document Type: Article
Times cited : (132)

References (53)
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    • Only a single example, synthesis of 3-phenylphthalide, was shown as an intramolecular variant in an NHC-catalyzed hydroacylation of activated ketones. See
    • Only a single example, synthesis of 3-phenylphthalide, was shown as an intramolecular variant in an NHC-catalyzed hydroacylation of activated ketones. See: Chan, A.; Scheidt, K. A. J. Am. Chem. Soc. 2006, 128, 4558
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    • During our investigations, Glorius and co-workers reported an example of NHC-catalyzed intramolecular cyclization of benzaldehydes bearing an unactivated alkyne moiety; see:;;, However, this reported reaction differs significantly from our work described herein in terms of reactivity under the conditions described, the product obtained, and the mechanistic pathway involved. The same group reported NHC-catalyzed hydroacylation of unactivated alkenes and arynes; see:;;; J. Am. Chem. Soc. 2009, 131, 14190
    • During our investigations, Glorius and co-workers reported an example of NHC-catalyzed intramolecular cyclization of benzaldehydes bearing an unactivated alkyne moiety; see: Biju, A. T.; Wurz, N. E.; Glorius, F. J. Am. Chem. Soc. 2010, 132, 5970 However, this reported reaction differs significantly from our work described herein in terms of reactivity under the conditions described, the product obtained, and the mechanistic pathway involved. The same group reported NHC-catalyzed hydroacylation of unactivated alkenes and arynes; see: Hirano, K.; Biju, A. T.; Piel, I.; Glorius, F. J. Am. Chem. Soc. 2009, 131, 14190
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    • For examples of NHC-catalyzed reactions involving esterification through a similar mechanism under aerobic conditions, see
    • For examples of NHC-catalyzed reactions involving esterification through a similar mechanism under aerobic conditions, see: Liu, Y.-K.; Li, R.; Yue, L.; Li, B.-J.; Chen, Y.-C.; Wu, Y.; Ding, L.-S. Org. Lett. 2006, 8, 1521
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    • 2 as an oxidant for NHC-catalyzed oxidation of aldehydes, see: Gu, L.; Zhang, Y. J. Am. Chem. Soc. 2010, 132, 914
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    • For selected examples of a base-promoted domino nucleophilic addition-cyclization reaction of 2-alkynylbenzaldehydes with alcohols, see
    • For selected examples of a base-promoted domino nucleophilic addition-cyclization reaction of 2-alkynylbenzaldehydes with alcohols, see: Dell'Acqua, M.; Facoetti, D.; Abbiati, G.; Rossi, E. Synthesis 2010, 2367
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.