메뉴 건너뛰기




Volumn 73, Issue 14, 2008, Pages 5452-5457

Three-component coupling using arynes and aminosilanes for ortho-selective double functionalization of aromatic skeletons

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; AROMATIC COMPOUNDS; ARSENIC COMPOUNDS; CARBONYLATION; CHEMICAL REACTIONS;

EID: 48249147369     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800761b     Document Type: Article
Times cited : (45)

References (54)
  • 2
    • 0000264238 scopus 로고
    • Trost,B. M, Fleming,I, Semmelhack,M. F, Eds, Pergamon: Oxford
    • (b) Kessar,S. V. In Comprehensive Organic Synthesis Trost,B. M. , Fleming,I. , Semmelhack,M. F. , Eds.; Pergamon: Oxford ,1991; Vol. 4, pp 483-515.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 483-515
    • Kessar, S.V.1
  • 8
    • 4544320921 scopus 로고    scopus 로고
    • Aryne-isocyanide-aldehyde: (a) Yoshida, H.; Fukushima, H.; Ohshita, J.; Kunai, A. Angew.Chem., Int. Ed. 2004, 43, 3935-3938.
    • Aryne-isocyanide-aldehyde: (a) Yoshida, H.; Fukushima, H.; Ohshita, J.; Kunai, A. Angew.Chem., Int. Ed. 2004, 43, 3935-3938.
  • 9
    • 7044231369 scopus 로고    scopus 로고
    • Aryne-isocyanideimine: (b) Yoshida, H.; Fukushima, H.; Ohshita, J.; Kunai, A. Tetrahedron Lett. 2004, 45, 8659-8662.
    • Aryne-isocyanideimine: (b) Yoshida, H.; Fukushima, H.; Ohshita, J.; Kunai, A. Tetrahedron Lett. 2004, 45, 8659-8662.
  • 10
    • 33748053357 scopus 로고    scopus 로고
    • 2: (c) Yoshida, H.; Fukushima, H.; Ohshita, J.; Kunai, A. J. Am. Chem. Soc. 2006, 128, 11040-11041.
    • 2: (c) Yoshida, H.; Fukushima, H.; Ohshita, J.; Kunai, A. J. Am. Chem. Soc. 2006, 128, 11040-11041.
  • 12
    • 0011646729 scopus 로고    scopus 로고
    • Formation of monosubstituted arenes by proton abstraction: (a) Sato, Y.; Toyooka, T.; Aoyama, T.; Shirai, H. J. Org. Chem. 1976, 41, 3559-3564.
    • Formation of monosubstituted arenes by proton abstraction: (a) Sato, Y.; Toyooka, T.; Aoyama, T.; Shirai, H. J. Org. Chem. 1976, 41, 3559-3564.
  • 17
    • 48249089135 scopus 로고    scopus 로고
    • For a review on insertion reactions of arynes into element-element σ-bond, see
    • For a review on insertion reactions of arynes into element-element σ-bond, see: Peña, D.; Pérez, D.; Guitián, E. Angew. Chem., Int. Ed. 2006, 45, 3578-3581.
    • (2006) Angew. Chem., Int. Ed , vol.45 , pp. 3578-3581
    • Peña, D.1    Pérez, D.2    Guitián, E.3
  • 31
    • 8744281396 scopus 로고    scopus 로고
    • Other three-component couplings using neutral nucleophiles: (a) Yoshida, H.; Watanabe, M.; Fukushima, H.; Ohshita, J.; Kunai, A. Org. Lett. 2004, 6, 4049-4051.
    • Other three-component couplings using neutral nucleophiles: (a) Yoshida, H.; Watanabe, M.; Fukushima, H.; Ohshita, J.; Kunai, A. Org. Lett. 2004, 6, 4049-4051.
  • 36
    • 0012397313 scopus 로고
    • The reaction of arynes with primary and secondary amines: (a) Snieckus, V
    • The reaction of arynes with primary and secondary amines: (a) Snieckus, V. Chem. Rev. 1990, 90, 879-933.
    • (1990) Chem. Rev , vol.90 , pp. 879-933
  • 38
    • 48249094862 scopus 로고    scopus 로고
    • The reaction of benzyne with benzaldehyde was reported to produce 2-(dimethylamino)benzhydrol (12% yield), whose dimethylamino moiety was derived from a benzyne precursor (1-(2-carboxyphenyl)-3,3-dimethyltriazene). However, this reaction was not developed as a useful synthetic procedure, because it required harsh conditions (160°C) and excess aldehyde (∼39 equiv). Nakayama, J.; Yoshida, M.; Shimamura, O. Chem. Lett. 1973, 451-454.
    • The reaction of benzyne with benzaldehyde was reported to produce 2-(dimethylamino)benzhydrol (12% yield), whose dimethylamino moiety was derived from a benzyne precursor (1-(2-carboxyphenyl)-3,3-dimethyltriazene). However, this reaction was not developed as a useful synthetic procedure, because it required harsh conditions (160°C) and excess aldehyde (∼39 equiv). Nakayama, J.; Yoshida, M.; Shimamura, O. Chem. Lett. 1973, 451-454.
  • 39
    • 33845560452 scopus 로고    scopus 로고
    • Similar products can be synthesized by the direct ortho-lithiation of anilides followed by reaction with an electrophile, although the highly basic reaction conditions would limit the use of substrates bearing relatively sensitive functional groups, a Fuhrer, W, and Gschwend, H. W. J. Org. Chem. 1979, 44, 1133-1136
    • Similar products can be synthesized by the direct ortho-lithiation of anilides followed by reaction with an electrophile, although the highly basic reaction conditions would limit the use of substrates bearing relatively sensitive functional groups. (a) Fuhrer, W.; and Gschwend, H. W. J. Org. Chem. 1979, 44, 1133-1136.
  • 43
    • 48249152880 scopus 로고    scopus 로고
    • The TMS group in aminosilylated product 8 was demonstrated to derive not from 1 but from 2a. See ref 3i
    • The TMS group in aminosilylated product 8 was demonstrated to derive not from 1 but from 2a. See ref 3i.
  • 44
    • 0348041998 scopus 로고    scopus 로고
    • A large amount of N,N-diethylaniline was formed as a byproduct in this reaction, which demonstrates an advantage of the use of aminosilanes in the three-component coupling. The existence of only a catalytic amount of amines, generated from aminosilanes and benzoic acid, in the reaction mixture would decrease aniline derivatives. For N-arylation of amines by the use of arynes, see: (a) Liu, Z.; Larock, R. C. Org. Lett. 2003, 5, 4673-4675.
    • A large amount of N,N-diethylaniline was formed as a byproduct in this reaction, which demonstrates an advantage of the use of aminosilanes in the three-component coupling. The existence of only a catalytic amount of amines, generated from aminosilanes and benzoic acid, in the reaction mixture would decrease aniline derivatives. For N-arylation of amines by the use of arynes, see: (a) Liu, Z.; Larock, R. C. Org. Lett. 2003, 5, 4673-4675.
  • 46
    • 0002516170 scopus 로고    scopus 로고
    • An amine and a silyl carboxylate are readily formed in the reaction of an aminosilane and a carboxylic acid: (a) Wissner, A. Tetrahedron Lett. 1978, 19, 2749-2752
    • An amine and a silyl carboxylate are readily formed in the reaction of an aminosilane and a carboxylic acid: (a) Wissner, A. Tetrahedron Lett. 1978, 19, 2749-2752.
  • 47
    • 84981839706 scopus 로고
    • (b) Ruhlmann, K. Chem. Ber. 1961, 94, 1876-1878.
    • (1961) Chem. Ber , vol.94 , pp. 1876-1878
    • Ruhlmann, K.1
  • 48
    • 48249113194 scopus 로고    scopus 로고
    • A reviewer pointed out that there may be an attractive hydrogen bonding between the amine H in 11 and an electrophile, which enhances the electrophilicity of 3 or 6.
    • A reviewer pointed out that there may be an attractive hydrogen bonding between the amine H in 11 and an electrophile, which enhances the electrophilicity of 3 or 6.
  • 49
    • 33645012569 scopus 로고    scopus 로고
    • Various alcohols are readily transformed into the respective silyl ethers via action with aminosilanes: (a) Shirini, F, Mollarazi, E. Synth. Commun. 2006, 36, 1109-1115
    • Various alcohols are readily transformed into the respective silyl ethers via action with aminosilanes: (a) Shirini, F.; Mollarazi, E. Synth. Commun. 2006, 36, 1109-1115.
  • 51
    • 48249139704 scopus 로고    scopus 로고
    • Because there was an excess of fluoride in the reaction mixture, three-component coupling products would exist as silicates, amides or alkoxides before a workup process. Therefore, we could only detect trace amounts of silyl ether 12 or silylamine 13 in crude products. For protodesilylation of silyl ethers with a fluoride ion, see: Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; John Wiley & Sons: New York, 1999; Chapter 2, pp 113-148.
    • Because there was an excess of fluoride in the reaction mixture, three-component coupling products would exist as silicates, amides or alkoxides before a workup process. Therefore, we could only detect trace amounts of silyl ether 12 or silylamine 13 in crude products. For protodesilylation of silyl ethers with a fluoride ion, see: Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; John Wiley & Sons: New York, 1999; Chapter 2, pp 113-148.
  • 52
    • 4544298756 scopus 로고    scopus 로고
    • Preferential nucleophilic attack at a para position of a chlorine atom also occurred in electrophilic coupling reactions of 4-chlorobenzyne: (a) Bunnett, J. F, Pyun, C. J. Org. Chem. 1969, 34, 2035-2037
    • Preferential nucleophilic attack at a para position of a chlorine atom also occurred in electrophilic coupling reactions of 4-chlorobenzyne: (a) Bunnett, J. F.; Pyun, C. J. Org. Chem. 1969, 34, 2035-2037.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.