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Volumn 12, Issue 23, 2010, Pages 5538-5541

On the validity of au-vinylidenes in the gold-catalyzed 1,2-migratory cycloisomerization of skipped propargylpyridines

Author keywords

[No Author keywords available]

Indexed keywords

GOLD; INDENE DERIVATIVE; MORPHINAN DERIVATIVE; N PROPARGYL; N-PROPARGYL; PYRIDINE; PYRIDINE DERIVATIVE; VINYL DERIVATIVE; VINYLINDENE;

EID: 78650360095     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1024794     Document Type: Article
Times cited : (87)

References (76)
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    • The B3LYP/6-31G*(LANL2DZ for Au and Br) method was used for all the calculations, and solvation effect was calculated by the CPCM model. See Supporting Information for details
    • The B3LYP/6-31G*(LANL2DZ for Au and Br) method was used for all the calculations, and solvation effect was calculated by the CPCM model. See Supporting Information for details.
  • 38
    • 78650331731 scopus 로고    scopus 로고
    • For examples of DFT calculations demonstrating the importance of the water molecule or water clusters in various catalytic reactions, see
    • For examples of DFT calculations demonstrating the importance of the water molecule or water clusters in various catalytic reactions, see
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    • See Supporting Information for details
    • See Supporting Information for details.
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    • For selected reviews on Au chemistry, see
    • For selected reviews on Au chemistry, see
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    • For a 1,2-H shift in Au-carbenes, see
    • For a 1,2-H shift in Au-carbenes, see
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    • 78650338902 scopus 로고    scopus 로고
    • 3 are similar to those for AuBr
    • 3 are similar to those for AuBr.
  • 56
    • 78650374993 scopus 로고    scopus 로고
    • In addition, DFT calculations showed that another alternative prototropic isomerization of the alkyne 1 into an allene is a reversible process requiring 18.5 kcal/mol activation free energy. No loss of the D-label was observed in 1b recovered from the Au-catalyzed cycloisomerization reaction at 50% conversion. On the basis of this, the allenization route can be ruled out. See Supporting Information for details
    • In addition, DFT calculations showed that another alternative prototropic isomerization of the alkyne 1 into an allene is a reversible process requiring 18.5 kcal/mol activation free energy. No loss of the D-label was observed in 1b recovered from the Au-catalyzed cycloisomerization reaction at 50% conversion. On the basis of this, the allenization route can be ruled out. See Supporting Information for details.
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    • 2O contradicts the concerted nature of the 1,2-H migrations suggested in the previous mechanistic rationale
    • 2O contradicts the concerted nature of the 1,2-H migrations suggested in the previous mechanistic rationale.
  • 58
    • 78650405085 scopus 로고    scopus 로고
    • For selected examples of a 1,2-Si migration over a 1,2-H shift to Au-carbene centers, see
    • For selected examples of a 1,2-Si migration over a 1,2-H shift to Au-carbene centers, see
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    • For 1,2-alkyl shifts to cationic centers, see:; Org. Lett. 2009, 11, 2293 Also see:; Angew. Chem., Int. Ed. 2007, 46, 5195
    • Sromek, A. W.; Rubina, M.; Gevorgyan, V. J. Am. Chem. Soc. 2005, 127, 10500 For 1,2-alkyl shifts to cationic centers, see: Davies, P. W.; Martin, N. Org. Lett. 2009, 11, 2293 Also see: Dudnik, A. S.; Gevorgyan, V. Angew. Chem., Int. Ed. 2007, 46, 5195
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 10500
    • Sromek, A.W.1    Rubina, M.2    Gevorgyan, V.3    Davies, P.W.4    Martin, N.5    Dudnik, A.S.6    Gevorgyan, V.7
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    • For selected examples of a transition-metal-catalyzed synthesis of indolizines, see
    • For selected examples of a transition-metal-catalyzed synthesis of indolizines, see


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.