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Volumn 25, Issue 8, 2006, Pages 1970-1977

Efficient and convenient synthesis of β-vinyl sulfides in nickel-catalyzed regioselective addition of thiols to terminal alkynes under solvent-free conditions

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CATALYSTS; CHEMICAL BONDS; NICKEL; SYNTHESIS (CHEMICAL);

EID: 33646373908     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om051105j     Document Type: Article
Times cited : (108)

References (77)
  • 5
    • 0003437149 scopus 로고
    • Studies in Organic Chemistry. V.19; Bernardi, F., Csizmadia, I. G., Mangini, A., Eds.; Elsevier: Amsterdam
    • (e) Organic Sulfur Chemistry. Theoretical and Experimental Advances; Studies in Organic Chemistry. V.19; Bernardi, F., Csizmadia, I. G., Mangini, A., Eds.; Elsevier: Amsterdam, 1985.
    • (1985) Organic Sulfur Chemistry. Theoretical and Experimental Advances
  • 47
    • 1342303394 scopus 로고    scopus 로고
    • For a related discussion of rate enhancement in the catalytic C-E (E = S, Se) bond formation reaction under solvent-free conditions see: Ananikov, V. P. ; Beletskaya, I. P. Org. Biomol. Chem. 2004, 2, 284.
    • (2004) Org. Biomol. Chem. , vol.2 , pp. 284
    • Ananikov, V.P.1    Beletskaya, I.P.2
  • 49
    • 33646359542 scopus 로고    scopus 로고
    • The selectivity of the addition reactions is reflected by the ratio of catalytic and noncatalytic products (2+5+6)7(3+4)
    • The selectivity of the addition reactions is reflected by the ratio of catalytic and noncatalytic products (2+5+6)7(3+4).
  • 50
    • 33646359300 scopus 로고    scopus 로고
    • note
    • It was shown that the isomerization reaction may proceed under transition metal-catalyzed, radical or photochemical conditions (refs 7 and 9). Therefore, different isomerization mechanisms may play the dominant role depending on reaction conditions and amount of catalyst.
  • 52
    • 33646374521 scopus 로고    scopus 로고
    • note
    • The E/Z ratio of anti-Markovnikov isomers was in the range 2:1-1:1. This suggests a radical nature of the side reaction.
  • 53
    • 33646384792 scopus 로고    scopus 로고
    • note
    • 6a-d). Trans and cis notations indicate the position of the R and R' groups.
  • 54
    • 33646373084 scopus 로고    scopus 로고
    • note
    • 1H NMR signals of 9 and 10 was accompanied with simultaneous increase in intensity of corresponding signals of 11 and 12. Therefore, 9 and 10 are the kinetic products of the syn-addition reaction.
  • 65
    • 33646336993 scopus 로고    scopus 로고
    • In agreement with proposed mechanism, no reaction took place in the absence of PhSH
    • In agreement with proposed mechanism, no reaction took place in the absence of PhSH.
  • 72
    • 33646353779 scopus 로고    scopus 로고
    • note
    • Catalyst activity depends on the amount of water in the reaction mixture. NMR monitoring (or GC) is the easiest way to determine appropriate reaction time.
  • 73
    • 33646351408 scopus 로고    scopus 로고
    • note
    • Unreacted PhSH can be easily recovered from the water phase by addition of aqueous HCl and extraction with hexane.
  • 76
    • 33646346227 scopus 로고    scopus 로고
    • note
    • In the studied system particle size and distribution depend on the sample preparation conditions. Therefore, these values obtained should be used as an estimation only.
  • 77
    • 33646349586 scopus 로고    scopus 로고
    • note
    • 1/2, where area is the area of the object.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.