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Volumn 67, Issue 26, 2002, Pages 9460-9463

Solid-phase synthesis of substituted alkynes using the Nicholas reaction

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; COBALT; ORGANIC ACIDS; ORGANIC POLYMERS; SYNTHESIS (CHEMICAL);

EID: 0344110754     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026156u     Document Type: Article
Times cited : (28)

References (32)
  • 1
    • 0035128271 scopus 로고    scopus 로고
    • For reviews on combinatorial chemistry and solid-phase synthesis, see: (a) Sammelson, R. E.; Kurth, M. J. Chem. Rev. 2001, 101, 137-202.
    • (2001) J. Chem. Rev. , vol.101 , pp. 137-202
    • Sammelson, R.E.1    Kurth, M.2
  • 3
    • 0003670259 scopus 로고    scopus 로고
    • Bannwarth, W., Felder, E., Eds.; Wiley-VCH: Weinheim, Germany
    • (c) Combinatorial Chemistry: A Practical Approach; Bannwarth, W., Felder, E., Eds.; Wiley-VCH: Weinheim, Germany, 2000
    • (2000) Combinatorial Chemistry: A Practical Approach
  • 9
    • 33845281351 scopus 로고
    • For reviews on the Nicholas reaction, see: (a) Nicholas, K. M. Acc. Chem. Res. 1987, 20, 207-214.
    • (1987) Acc. Chem. Res. , vol.20 , pp. 207-214
    • Nicholas, K.M.1
  • 10
    • 0000134381 scopus 로고
    • Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Elsevier Science Ltd.: Oxford UK, Chapter 7.1
    • (b) Caffyn, A.; Nicholas, K. M. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Elsevier Science Ltd.: Oxford, UK, 1995; Vol. 12, Chapter 7.1, pp 685-702.
    • (1995) Comprehensive Organometallic Chemistry , vol.12 , pp. 685-702
    • Caffyn, A.1    Nicholas K.M. II2
  • 14
    • 0025278269 scopus 로고
    • For Pauson-Khand approaches using polymer-bound substrates, see: (a) Schore, N. E.; Najdi, S. D. J. Am. Chem. Soc. 1990, 112, 441-442.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 441-442
    • Schore, N.E.1    Najdi, S.D.2
  • 22
    • 0000509322 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press, New York, Chapter 24
    • (b) Sonogashira, K. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 3, Chapter 2.4, pp 521-549.
    • (1991) Comprehensive Organic Chemistry , vol.3 , pp. 521-549
    • Sonogashira, K.1
  • 23
    • 0347781343 scopus 로고    scopus 로고
    • note
    • 18 h is generally sufficient for this step, only in the case of the quarternary alkynol 2-phenyl-3-butyn-2-ol was the loading increased if the reaction was left for 48 h.
  • 25
    • 0027378315 scopus 로고
    • Piperidine has been found to be more efficient than other amines in the Sonogashira coupling of aliphatic alkynes and aryl iodides, see: (a) Alami, M.; Ferri, F.; Linstrumelle, G. Tetrahedron Lett. 1993, 34, 6403-6406. (b) Kilså, K.; Kajanus, J.; Mårtensson, J.; Albinsson, B. J. Phys. Chem. B 1999, 103, 7329-7339.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 6403-6406
    • Alami, M.1    Ferri, F.2    Linstrumelle, G.3
  • 26
    • 0001050778 scopus 로고    scopus 로고
    • Piperidine has been found to be more efficient than other amines in the Sonogashira coupling of aliphatic alkynes and aryl iodides, see: (a) Alami, M.; Ferri, F.; Linstrumelle, G. Tetrahedron Lett. 1993, 34, 6403-6406. (b) Kilså, K.; Kajanus, J.; Mårtensson, J.; Albinsson, B. J. Phys. Chem. B 1999, 103, 7329-7339.
    • (1999) J. Phys. Chem. B , vol.103 , pp. 7329-7339
    • Kilså, K.1    Kajanus, J.2    Mårtensson, J.3    Albinsson, B.4
  • 27
    • 0345890065 scopus 로고    scopus 로고
    • note
    • -1.
  • 30
    • 0347781342 scopus 로고    scopus 로고
    • note
    • The ortho and para isomers can be separated before the CAN-decomplexation step.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.