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Volumn 79, Issue 17, 2014, Pages 8110-8117

Copper-catalyzed decarboxylative sulfonylation of α,β-unsaturated carboxylic acids

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHELATION; LIGANDS;

EID: 84924338373     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo501314y     Document Type: Article
Times cited : (55)

References (69)
  • 55
    • 84924310358 scopus 로고    scopus 로고
    • In most of the examples (Table 2), the reaction did not go to completion. As a result, we observed that the acid precursors were present even after an extended reaction time. Interestingly, scale-up experiments resulted in the formation of product (3g) in better yield (Scheme 3)
    • In most of the examples (Table 2), the reaction did not go to completion. As a result, we observed that the acid precursors were present even after an extended reaction time. Interestingly, scale-up experiments resulted in the formation of product (3g) in better yield (Scheme 3).
  • 56
    • 74349121600 scopus 로고    scopus 로고
    • Free hydroxy group is known to quench the radical intermediate. Therefore, we believe that substrates such as (E)-3-(4-hydroxyphenyl)acrylic acid do not undergo a facile decarboxylation. We believe on similar note that the compounds with free amino groups such as (E)-3-(1 H -indol-3-yl)acrylic acid and (E)-3-(4-aminophenyl)acrylic acid are inert under the reaction conditions. Further, the decarboxylation of the substrates such as 2-(4-methoxyphenyl)acrylic acid, (E)-3-(4-methoxyphenoxy)acrylic acid, (E)-4-(4-methoxyphenyl)-4-oxobut-2-enoic acid, 2-(4-methoxyphenyl)acetic acid, 4-methoxybenzoic acid, and 1-benzylpyrrolidine-2-carboxylic are difficult and need harsh reaction conditions See
    • Free hydroxy group is known to quench the radical intermediate. Therefore, we believe that substrates such as (E)-3-(4-hydroxyphenyl)acrylic acid do not undergo a facile decarboxylation. We believe on similar note that the compounds with free amino groups such as (E)-3-(1 H -indol-3-yl)acrylic acid and (E)-3-(4-aminophenyl)acrylic acid are inert under the reaction conditions. Further, the decarboxylation of the substrates such as 2-(4-methoxyphenyl)acrylic acid, (E)-3-(4-methoxyphenoxy)acrylic acid, (E)-4-(4-methoxyphenyl)-4-oxobut-2-enoic acid, 2-(4-methoxyphenyl)acetic acid, 4-methoxybenzoic acid, and 1-benzylpyrrolidine-2-carboxylic are difficult and need harsh reaction conditions See: Nishida, Y.; Yamashita, E.; Miki, W. Carotenoid Sci. 2007, 11, 16
    • (2007) Carotenoid Sci. , vol.11 , pp. 16
    • Nishida, Y.1    Yamashita, E.2    Miki, W.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.