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Volumn 13, Issue 2, 2011, Pages 208-211

Rhodium(I)-catalyzed addition of arylboronic acids to (benzyl-/ arylsulfonyl)acetonitriles: Efficient synthesis of (Z)-β- sulfonylvinylamines and β-Keto sulfones

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE DERIVATIVE; BORONIC ACID DERIVATIVE; RHODIUM; SULFONE;

EID: 78651497945     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102598p     Document Type: Article
Times cited : (92)

References (59)
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    • For reviews, see
    • For reviews, see
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    • Palladium-catalyzed reactions
    • Palladium-catalyzed reactions
  • 15
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    • For reviews on Rh-catalyzed C-C bond formations, see
    • For reviews on Rh-catalyzed C-C bond formations, see
  • 22
    • 0032542313 scopus 로고    scopus 로고
    • In this Rh-catalyzed addition of phenylboronic acid to 4-cyanobenzaldehyde, the cyano group remains intact while the secondary alcohol product is formed via addition to the aldehyde group in high yield
    • Sakai, M.; Ueda, M.; Miyaura, N. Angew. Chem., Int. Ed. 1998, 37, 3279 In this Rh-catalyzed addition of phenylboronic acid to 4-cyanobenzaldehyde, the cyano group remains intact while the secondary alcohol product is formed via addition to the aldehyde group in high yield.
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 3279
    • Sakai, M.1    Ueda, M.2    Miyaura, N.3
  • 29
    • 78651508715 scopus 로고    scopus 로고
    • Applications of β-keto sulfones
    • Applications of β-keto sulfones
  • 35
    • 78651505866 scopus 로고    scopus 로고
    • For descriptions of sulfone chemistry, see
    • For descriptions of sulfone chemistry, see
  • 40
    • 78449258085 scopus 로고    scopus 로고
    • We have observed activating/directing effects of the sulfone group in Rh(I)-catalyzed addition of arylboronic acids to allyl sulfones
    • We have observed activating/directing effects of the sulfone group in Rh(I)-catalyzed addition of arylboronic acids to allyl sulfones: Tsui, G. C.; Lautens, M. Angew. Chem., Int. Ed. 2010, 49, 8938
    • (2010) Angew. Chem., Int. Ed. , vol.49 , pp. 8938
    • Tsui, G.C.1    Lautens, M.2
  • 41
    • 78651478496 scopus 로고    scopus 로고
    • 3N, product 2a slightly hydrolyzed on column to form a small amount of 3a (2a: 3a = 20:1)
    • 3N, product 2a slightly hydrolyzed on column to form a small amount of 3a (2a: 3a = 20:1).
  • 46
    • 78651480714 scopus 로고    scopus 로고
    • For applications of heteroaromatic sulfones, see
    • For applications of heteroaromatic sulfones, see
  • 50
    • 78651519907 scopus 로고    scopus 로고
    • Similar results were observed in our studies of additions to allyl sulfones (ref 10) using the same catalyst. The benzothiazolyl sulfone gave poor conversion, possibly due to poisoning of the rhodium catalyst. The phenyltetrazolyl sulfone led to decomposition under the reaction conditions
    • Similar results were observed in our studies of additions to allyl sulfones (ref 10) using the same catalyst. The benzothiazolyl sulfone gave poor conversion, possibly due to poisoning of the rhodium catalyst. The phenyltetrazolyl sulfone led to decomposition under the reaction conditions.
  • 51
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    • For selected recent reports, see
    • For selected recent reports, see
  • 59
    • 78651516055 scopus 로고    scopus 로고
    • X-ray crystal structure of 5b confirmed the Z -alkene geometry (see the Supporting Information)
    • X-ray crystal structure of 5b confirmed the Z -alkene geometry (see the Supporting Information).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.