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Volumn 26, Issue 24, 2007, Pages 5778-5781

Catalytic alkyne hydrothiolation with alkanethiols using Wilkinson's catalyst

Author keywords

[No Author keywords available]

Indexed keywords

BIOACTIVITY; CATALYST ACTIVITY; DEUTERIUM COMPOUNDS; MOLECULAR BIOLOGY; REDOX REACTIONS; SULFUR COMPOUNDS;

EID: 36749052170     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om700811e     Document Type: Article
Times cited : (98)

References (69)
  • 2
    • 28744458623 scopus 로고    scopus 로고
    • Angew. Chem., Int. Ed. 2005, 44, 7674-7684.
    • (2005) Chem., Int. Ed , vol.44 , pp. 7674-7684
    • Angew1
  • 20
    • 0000898678 scopus 로고    scopus 로고
    • Radical methods provide a mixture of the E- and Z-linear regioisomers (A and B, eq 1), generally favoring the Z isomer (B). For example, see: (a) Benati, L.; Capella, L.; Montevecchi, P. C.; Spagnolo, P. J. Org. Chem. 1994, 59, 2818-2823.
    • Radical methods provide a mixture of the E- and Z-linear regioisomers (A and B, eq 1), generally favoring the Z isomer (B). For example, see: (a) Benati, L.; Capella, L.; Montevecchi, P. C.; Spagnolo, P. J. Org. Chem. 1994, 59, 2818-2823.
  • 23
    • 0032541643 scopus 로고    scopus 로고
    • For an example of a radical reaction leading to the E/Z mixtures enriched in the E-linear isomer, see: Nguyen, V.-H.; Nishino, H.; Kajikawa, S.; Kurosawa, K. Tetrahedron 1998, 54, 11445-11460.
    • For an example of a radical reaction leading to the E/Z mixtures enriched in the E-linear isomer, see: Nguyen, V.-H.; Nishino, H.; Kajikawa, S.; Kurosawa, K. Tetrahedron 1998, 54, 11445-11460.
  • 24
    • 29344451759 scopus 로고    scopus 로고
    • Nucleophilic methods have been used to prepare alkyl (Z)-vinyl sulfides: (a) Carson, J. F.; Boggs, L. E. J. Org. Chem. 1967, 32, 673-676.
    • Nucleophilic methods have been used to prepare alkyl (Z)-vinyl sulfides: (a) Carson, J. F.; Boggs, L. E. J. Org. Chem. 1967, 32, 673-676.
  • 26
    • 0001664696 scopus 로고    scopus 로고
    • Metal-catalyzed hydrothiolation reactions with arenethiols are reported as follows. Pd: (a) Kuniyasu, H.; Ogawa, A.; Sato, K.-I.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 5902-5903.
    • Metal-catalyzed hydrothiolation reactions with arenethiols are reported as follows. Pd: (a) Kuniyasu, H.; Ogawa, A.; Sato, K.-I.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 5902-5903.
  • 30
    • 33746893062 scopus 로고    scopus 로고
    • Yoshiyuki, M.; Seino, H.; Mizobe, Y. J. Organomet. Chem. 2006, 691, 3157-3164. Ni:
    • (e) Yoshiyuki, M.; Seino, H.; Mizobe, Y. J. Organomet. Chem. 2006, 691, 3157-3164. Ni:
  • 35
    • 33751156297 scopus 로고    scopus 로고
    • For an example of hydrothiolation of highly activated alkynes (Michael acceptors) using alkanethiols, see: Koelle, U.; Rietmann, C.; Tjoe, J.; Wagner, T.; Englert, U. Organometallics 1995, 14, 703-713.
    • For an example of hydrothiolation of highly activated alkynes (Michael acceptors) using alkanethiols, see: Koelle, U.; Rietmann, C.; Tjoe, J.; Wagner, T.; Englert, U. Organometallics 1995, 14, 703-713.
  • 36
    • 0033936116 scopus 로고    scopus 로고
    • For an example of intramolecular alkyne hydrothiolation with alkanethiols, see
    • For an example of intramolecular alkyne hydrothiolation with alkanethiols, see: McDonald, F. E.; Burova, S. A.; Huffman, L. G. Synthesis 2000, 7, 970-974.
    • (2000) Synthesis , vol.7 , pp. 970-974
    • McDonald, F.E.1    Burova, S.A.2    Huffman, L.G.3
  • 38
    • 34147123642 scopus 로고    scopus 로고
    • Pd-catalyzed hydrothiolation using alkanethiols: (a) Kondoh, A.; Yirimitsu, H.; Oshima, K. Org. Lett. 2007, 9, 1383-1385.
    • Pd-catalyzed hydrothiolation using alkanethiols: (a) Kondoh, A.; Yirimitsu, H.; Oshima, K. Org. Lett. 2007, 9, 1383-1385.
  • 46
    • 36749025603 scopus 로고    scopus 로고
    • 2
    • 2
  • 49
    • 0000793706 scopus 로고    scopus 로고
    • Methoxypalladation: Stille, J. K.; James, D. E.; Hines, L. F. J. Am. Chem. Soc. 1973, 95, 5062-5064.
    • (a) Methoxypalladation: Stille, J. K.; James, D. E.; Hines, L. F. J. Am. Chem. Soc. 1973, 95, 5062-5064.
  • 50
    • 36748999300 scopus 로고    scopus 로고
    • Hydroxypalladation: Stille, J. K.; James, D. E. J. Am. Chem. Soc. 1975, 97, 614-616. Aminopalladation:
    • (b) Hydroxypalladation: Stille, J. K.; James, D. E. J. Am. Chem. Soc. 1975, 97, 614-616. Aminopalladation:
  • 56
    • 0038651053 scopus 로고    scopus 로고
    • Canepa, G.; Brandt, C. D.; Hg, K.; Wolf, J.; Werner. H. Chem. Eur. J. 2003, 9, 2502-2515.
    • (c) Canepa, G.; Brandt, C. D.; Hg, K.; Wolf, J.; Werner. H. Chem. Eur. J. 2003, 9, 2502-2515.
  • 57
    • 36749047871 scopus 로고    scopus 로고
    • No evidence of deuterium exchange between alkyne and thiol was observed
    • No evidence of deuterium exchange between alkyne and thiol was observed.
  • 58
    • 36749044705 scopus 로고    scopus 로고
    • Thiol and alkyne were allowed to react in the absence of Wilkinson's catalyst to 54% conversion (38% Z and 16% E). Catalyst was then added. The reaction proceeded to 92% conversion (38% Z, 52% E, 2% branched), consistent with our data that the catalytic reaction proceeds with 19:1 E:branched selectivity.
    • Thiol and alkyne were allowed to react in the absence of Wilkinson's catalyst to 54% conversion (38% Z and 16% E). Catalyst was then added. The reaction proceeded to 92% conversion (38% Z, 52% E, 2% branched), consistent with our data that the catalytic reaction proceeds with 19:1 E:branched selectivity.
  • 61
    • 0033576668 scopus 로고    scopus 로고
    • Angew. Chem., Int. Ed. 1999, 38, 3689-3691.
    • (1999) Chem., Int. Ed , vol.38 , pp. 3689-3691
    • Angew1
  • 65
    • 0013272402 scopus 로고    scopus 로고
    • Togni, A, Grützmacher, H, Eds, Wiley-VCH: Weinheim, Germany
    • (b) Catalytic Heterofunctionalization; Togni, A., Grützmacher, H., Eds.; Wiley-VCH: Weinheim, Germany, 2001.
    • (2001) Catalytic Heterofunctionalization


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.