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Volumn 47, Issue 13, 2008, Pages 2407-2410

Efficient oxidative alkyne homocoupling catalyzed by a monomeric dicopper-substituted silicotungstate

Author keywords

Alkynes; Copper; Homocoupling; Homogeneous catalysis; Polyoxometalates

Indexed keywords

CHEMICAL REACTIONS; HYDROCARBONS;

EID: 42449149114     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200705126     Document Type: Article
Times cited : (189)

References (56)
  • 8
    • 84902422242 scopus 로고    scopus 로고
    • Eds, J. A. McCleverty, T. J. Meyer, Elsevier Science, New York
    • h) C. L. Hill in Comprehensive Coordination Chemistry II, Vol. 4 (Eds.: J. A. McCleverty, T. J. Meyer), Elsevier Science, New York, 2004, p. 679;
    • (2004) Comprehensive Coordination Chemistry II , vol.4 , pp. 679
    • Hill, C.L.1
  • 46
    • 53549109793 scopus 로고    scopus 로고
    • An equimolar amount of benzamide (formed by the hydration of benzonitrile) with respect to the corresponding diyne was formed
    • An equimolar amount of benzamide (formed by the hydration of benzonitrile) with respect to the corresponding diyne was formed.
  • 47
    • 53549122325 scopus 로고    scopus 로고
    • When the oxidative coupling of 1a in DMF was carried out in the presence of stoichiometric amounts of benzonitrile with respect to the amount of water formed, an 88% yield of 2a was obtained after 24 h (cf. 63% yield without benzonitrile). In addition, the reaction of 1a with 4-Å molecular sieves (200 mg, pretreated at 423 K) in DMF or DMSO gave 2a in 90 and 86% yields, respectively, under the conditions in Table 1. These results show that benzonitrile is not a special solvent and that various other solvents can be used for this coupling reaction in the presence of water scavengers.
    • When the oxidative coupling of 1a in DMF was carried out in the presence of stoichiometric amounts of benzonitrile with respect to the amount of water formed, an 88% yield of 2a was obtained after 24 h (cf. 63% yield without benzonitrile). In addition, the reaction of 1a with 4-Å molecular sieves (200 mg, pretreated at 423 K) in DMF or DMSO gave 2a in 90 and 86% yields, respectively, under the conditions in Table 1. These results show that benzonitrile is not a special solvent and that various other solvents can be used for this coupling reaction in the presence of water scavengers.
  • 50
    • 53549098635 scopus 로고    scopus 로고
    • The length of the induction period is dependent on the concentration of I and 1a. Thus, a decrease in the concentration of I and 1a results in a lengthening of the induction period. An induction period of approximately 50 min is observed when the catalytic aerobic homocoupling of 1a is carried out under the conditions in Figure 2 see the Supporting Information
    • The length of the induction period is dependent on the concentration of I and 1a. Thus, a decrease in the concentration of I and 1a results in a lengthening of the induction period. An induction period of approximately 50 min is observed when the catalytic aerobic homocoupling of 1a is carried out under the conditions in Figure 2 (see the Supporting Information).
  • 51
    • 53549099467 scopus 로고    scopus 로고
    • No reaction of internal alkynes such as diphenylacetylene and 2-octyne occurs in the presence of I, thereby suggesting that the copper species in I is terminally bound to an alkyne.
    • No reaction of internal alkynes such as diphenylacetylene and 2-octyne occurs in the presence of I, thereby suggesting that the copper species in I is terminally bound to an alkyne.
  • 55
    • 0032045174 scopus 로고    scopus 로고
    • It has been reported that absorption bands due to alkynylcopper species can be observed around 370 nm. No absorption bands could be detected here, however, because of overlap with the intense absorption bands of I, solvent, and products: V. W. Yam, K. K. Lo, W. K. Fung, C. Wang, Coord. Chem. Rev. 1998, 171, 17
    • It has been reported that absorption bands due to alkynylcopper species can be observed around 370 nm. No absorption bands could be detected here, however, because of overlap with the intense absorption bands of I, solvent, and products: V. W. Yam, K. K. Lo, W. K. Fung, C. Wang, Coord. Chem. Rev. 1998, 171, 17.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.