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Volumn 130, Issue 43, 2008, Pages 14082-14083

Synthesis of 1,2- and 1,3-dicarboxylic acids via Pd(II)-catalyzed carboxylation of aryl and vinyl C-H bonds

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DICARBOXYLIC ACID; 1,3 DICARBOXYLIC ACID; CARBON; CARBOXYLIC ACID DERIVATIVE; LEAD; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

EID: 54849420705     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja8063827     Document Type: Article
Times cited : (334)

References (42)
  • 7
    • 54849409172 scopus 로고    scopus 로고
    • 2, see: (d) Itahara, T. Chem. Lett. 1982, 11, 1151-1152.
    • 2, see: (d) Itahara, T. Chem. Lett. 1982, 11, 1151-1152.
  • 8
  • 10
    • 77749235787 scopus 로고
    • For the carbonylation of palladacycles, see: g
    • For the carbonylation of palladacycles, see: (g) Ryabov, A. D. Synthesis 1985, 233-252.
    • (1985) Synthesis , pp. 233-252
    • Ryabov, A.D.1
  • 11
    • 0343535251 scopus 로고
    • For the carbonylation of C-H bonds by other metals, see: a
    • For the carbonylation of C-H bonds by other metals, see: (a) Mori, Y.; Tsuji, J. Tetrahedron 1971, 27, 3811-3819.
    • (1971) Tetrahedron , vol.27 , pp. 3811-3819
    • Mori, Y.1    Tsuji, J.2
  • 19
    • 3242659209 scopus 로고    scopus 로고
    • 2 insertion process for carboxylation, see: Whisler, M. C.; MacNeil, S.; Snieckus, V.; Beak, P. Angew. Chem., Int. Ed. 2004, 43, 2206-2225.
    • 2 insertion process for carboxylation, see: Whisler, M. C.; MacNeil, S.; Snieckus, V.; Beak, P. Angew. Chem., Int. Ed. 2004, 43, 2206-2225.
  • 22
    • 0025871267 scopus 로고
    • For other works on carboxyl-directed C-H bond activation, see: a
    • For other works on carboxyl-directed C-H bond activation, see: (a) Kao, L.-C.; Sen, A. J. Chem. Soc. Chem. Commun. 1991, 1242-1243.
    • (1991) J. Chem. Soc. Chem. Commun , pp. 1242-1243
    • Kao, L.-C.1    Sen, A.2
  • 31
    • 54849436038 scopus 로고    scopus 로고
    • Phenylacetic and α-methyl phenylacetic acids give <10% products
    • Phenylacetic and α-methyl phenylacetic acids give <10% products.
  • 33
    • 34347214018 scopus 로고    scopus 로고
    • For a recent example of vinylic C-H bond activation, see: a
    • For a recent example of vinylic C-H bond activation, see: (a) Lu, J.; Tan, X.; Chen, C. J. Am. Chem. Soc. 2007, 129, 7768-7769.
    • (2007) J. Am. Chem. Soc , vol.129 , pp. 7768-7769
    • Lu, J.1    Tan, X.2    Chen, C.3
  • 34
    • 54849414621 scopus 로고    scopus 로고
    • The α-aryl ring is necessary for the vinyl C-H carboxylation. Carboxylation at the ortho-aryl C-H bond was not observed
    • (b) The α-aryl ring is necessary for the vinyl C-H carboxylation. Carboxylation at the ortho-aryl C-H bond was not observed.
  • 37
    • 54849433122 scopus 로고    scopus 로고
    • Palladacycles are usually observed in dimeric or trinuclear forms in absence of external ligands: (a) Reference 2g.
    • Palladacycles are usually observed in dimeric or trinuclear forms in absence of external ligands: (a) Reference 2g.
  • 39
    • 0035833296 scopus 로고    scopus 로고
    • For the synthesis of a similar complex from o-halobenzoic acids, see: (a) Fernandez-Rivas, C.; Cardenas, D. J.; Martin-Matute, B.; Monge, A.; Gutierrez-Puebla, E.; Echavarren, A. M. Organometallics 2001, 20, 2998-3006.
    • For the synthesis of a similar complex from o-halobenzoic acids, see: (a) Fernandez-Rivas, C.; Cardenas, D. J.; Martin-Matute, B.; Monge, A.; Gutierrez-Puebla, E.; Echavarren, A. M. Organometallics 2001, 20, 2998-3006.
  • 41
    • 54849413559 scopus 로고    scopus 로고
    • Evidence for in situ hydrolysis under catalytic conditions is as follows: (a) early termination of the reaction of 1 gave a mixture of anhydride 1f and dicarboxylic acid 1a.
    • Evidence for in situ hydrolysis under catalytic conditions is as follows: (a) early termination of the reaction of 1 gave a mixture of anhydride 1f and dicarboxylic acid 1a.
  • 42
    • 54849439920 scopus 로고    scopus 로고
    • In a separate experiment, the anhydride 1f was converted into dicarboxylic acid 1a under the catalytic conditions
    • (b) In a separate experiment, the anhydride 1f was converted into dicarboxylic acid 1a under the catalytic conditions.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.