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Volumn 10, Issue 12, 2008, Pages 2509-2512

Orthoplatinated triarylphosphite as a highly efficient catalyst for addition reactions of arylboronic acids with aldehydes: Low catalyst loading catalysis and a new tandem reaction sequence

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; BORONIC ACID DERIVATIVE; ORGANOPHOSPHORUS COMPOUND; PLATINUM COMPLEX; PROPANOL;

EID: 48849096555     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800774c     Document Type: Article
Times cited : (66)

References (86)
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    • Just before the submission of our manuscript, Kuriyama and co-worker reported the Pd/N-heterocyclic imidazolium salt-catalyzed addition reaction of phenylboronic acid with benzaldehyde with 0.05% catalyst loading in 99% yield. Further decreasing the catalyst loading led to a significant yield drop (54%), suggesting the catalyst decomposition likely occurred through reductive elimination to prevent the reaction from completion. See: Kuriyama, M.; Shimazawa, R.; Shirai, R. J. Org. Chem. 2008, 73, 1597-1600.
    • Just before the submission of our manuscript, Kuriyama and co-worker reported the Pd/N-heterocyclic imidazolium salt-catalyzed addition reaction of phenylboronic acid with benzaldehyde with 0.05% catalyst loading in 99% yield. Further decreasing the catalyst loading led to a significant yield drop (54%), suggesting the catalyst decomposition likely occurred through reductive elimination to prevent the reaction from completion. See: Kuriyama, M.; Shimazawa, R.; Shirai, R. J. Org. Chem. 2008, 73, 1597-1600.
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    • 1,3-Diaryl-1-propanols are a common structural unit for a number of biologically active compounds or intermediates for the preparation of biologically active compounds. For examples see: (a) Gunn, D.; Akuche, C.; Baryza, J.; Blue, M.-L.; Brennan, C.; Campbell, A.-M.; Choi, S.; Cook, J.; Conrad, P.; Dixon, B.; Dumas, J.; Ehrlich, P.; Gane, T.; Joe, T.; Johnson, J.; Jordan, J.; Kramss, R.; Liu, P.; Levy, J.; Lowe, D.; McAlexander, I.; Natero, R.; Redman, A. M.; Scott, W.; Seng, T.; Sibley, R.; Wang, M.; Wang, Y.; Wood, J.; Zhang, Z. Bioorg. Med. Chem. Lett. 2005, 15, 3053-3057.
    • 1,3-Diaryl-1-propanols are a common structural unit for a number of biologically active compounds or intermediates for the preparation of biologically active compounds. For examples see: (a) Gunn, D.; Akuche, C.; Baryza, J.; Blue, M.-L.; Brennan, C.; Campbell, A.-M.; Choi, S.; Cook, J.; Conrad, P.; Dixon, B.; Dumas, J.; Ehrlich, P.; Gane, T.; Joe, T.; Johnson, J.; Jordan, J.; Kramss, R.; Liu, P.; Levy, J.; Lowe, D.; McAlexander, I.; Natero, R.; Redman, A. M.; Scott, W.; Seng, T.; Sibley, R.; Wang, M.; Wang, Y.; Wood, J.; Zhang, Z. Bioorg. Med. Chem. Lett. 2005, 15, 3053-3057.
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    • We found 4 was an excellent catalyst for the 1,4-addition of arylboronic acid with α,β-unsaturated ketones; see the Supporting Information.
    • We found 4 was an excellent catalyst for the 1,4-addition of arylboronic acid with α,β-unsaturated ketones; see the Supporting Information.
  • 86
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    • The addition of phenylboronic acid with chalcone catalyzed by 4 (5% 4, room temperature, 1 h, 71% conversion) was recently reported; see ref 9
    • The addition of phenylboronic acid with chalcone catalyzed by 4 (5% 4, room temperature, 1 h, 71% conversion) was recently reported; see ref 9.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.