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Volumn 48, Issue 33, 2009, Pages 6148-6151

Electrophilic activation of benzaldehydes through ortho palladation: One-pot synthesis of 3-methylene-indan-1-ols through a domino allylstannylation/heck reaction under neutral conditions

Author keywords

Allylation; Domino reactions; Heck reaction; Palladium; Stannaries

Indexed keywords

ALKYLIDENES; ALLYLATION; ALLYLTRIBUTYLSTANNANE; CATALYTIC ACTIVATION; CATALYZED REACTIONS; DOMINO REACTIONS; ELECTROPHILIC ACTIVATION; HECK REACTION; LEWIS ACIDIC; NEUTRAL CONDITIONS; ONE-POT SYNTHESIS; ORTHO POSITION; OXIDATIVE ADDITIONS; PALLADATION; REACTION UNDER; STANNARIES;

EID: 70349902652     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200901837     Document Type: Article
Times cited : (30)

References (38)
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    • After aqueous extractive workup (MTBE) and removal of all volatiles in vacuo, the crude triflates 14 were obtained with ≥ 95% purity (GC-MS).
    • After aqueous extractive workup (MTBE) and removal of all volatiles in vacuo, the crude triflates 14 were obtained with ≥ 95% purity (GC-MS).
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    • 1H NMR analysis (500 MHz) revealed the formation of a second aldehyde species indicated by a singlet at δ = 10.50 ppm in low concentration besides the starting material 6 (10.25 ppm). The assignments were supported by two-dimensional correlation spectra. Species related to 17 have been structurally characterized; see: J. Vicente, J.-A. Abad, E. Martínez-Viviente, B. M. C. Ramírez de Arellano, Organometallics 2000, 19, 752-760.
    • 1H NMR analysis (500 MHz) revealed the formation of a second aldehyde species indicated by a singlet at δ = 10.50 ppm in low concentration besides the starting material 6 (10.25 ppm). The assignments were supported by two-dimensional correlation spectra. Species related to 17 have been structurally characterized; see: J. Vicente, J.-A. Abad, E. Martínez-Viviente, B. M. C. Ramírez de Arellano, Organometallics 2000, 19, 752-760.
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    • Only when ortho-bromobenzaldehydes (in contrast to the corresponding iodides and triflates) were used as substrates, were small amounts of byproducts arising from primary allylation of the aldehyde function observed.
    • Only when ortho-bromobenzaldehydes (in contrast to the corresponding iodides and triflates) were used as substrates, were small amounts of byproducts arising from primary allylation of the aldehyde function observed.
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    • a Lewis acid type activation in the palladium(II)-catalyzed allylation of aldehydes by allyltributylstannane seems to be much more favorable than alternative pathways via allyl-palladium intermediates; see: b) O. Piechaczyk, T. Cantat, N. Mezailles, P. Le Floch, J. Org. Chem. 2007, 72, 4228-4237.
    • a Lewis acid type activation in the palladium(II)-catalyzed allylation of aldehydes by allyltributylstannane seems to be much more favorable than alternative pathways via allyl-palladium intermediates; see: b) O. Piechaczyk, T. Cantat, N. Mezailles, P. Le Floch, J. Org. Chem. 2007, 72, 4228-4237.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.