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Volumn 48, Issue 30, 2009, Pages 5534-5537

Gold-catalyzed cycloaromatization of 2, 4-dien-6-yne carboxylic acids: Synthesis of 2, 3-disubstituted phenols and unsymmetrical Bi- and terphenyls

Author keywords

Cycloaromatization; Gold; Homogeneous catalysis; Phenols; Terphenyls

Indexed keywords

CATALYST LOADINGS; CYCLOAROMATIZATION; ELECTRON-DONATING GROUP; HOMOGENEOUS CATALYSIS; REGIO-SELECTIVE; ROOM TEMPERATURE; TERPHENYLS; TRIPLE BONDS; UNSYMMETRICAL;

EID: 70349911558     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200901269     Document Type: Article
Times cited : (50)

References (49)
  • 1
    • 70349945822 scopus 로고    scopus 로고
    • For recent reviews on the Bergman, Saito-Myers, and Moore cyclizations, see
    • For recent reviews on the Bergman, Saito-Myers, and Moore cyclizations, see
  • 4
    • 0000770422 scopus 로고    scopus 로고
    • K. K. Wang, Chem. Rev. 1996, 96, 207-222;
    • (1996) Chem. Rev , vol.96 , pp. 207-222
    • Wang, K.K.1
  • 7
    • 0029860625 scopus 로고    scopus 로고
    • Ru: a C. A. Merlic, M. E. Pauly, J. Am. Chem. Soc. 1996, 118, 11319-11320;
    • Ru: a) C. A. Merlic, M. E. Pauly, J. Am. Chem. Soc. 1996, 118, 11319-11320;
  • 10
    • 0035920887 scopus 로고    scopus 로고
    • Rh: a J. W. Dankwardt, Tetrahedron Lett. 2001, 42, 5809-5812;
    • Rh: a) J. W. Dankwardt, Tetrahedron Lett. 2001, 42, 5809-5812;
  • 13
    • 33846689405 scopus 로고    scopus 로고
    • S. P. Nolan, Nature 2007, 445, 496-497.
    • (2007) Nature , vol.445 , pp. 496-497
    • Nolan, S.P.1
  • 14
    • 70349952730 scopus 로고    scopus 로고
    • For recent reviews, see
    • For recent reviews, see
  • 17
    • 51249100498 scopus 로고    scopus 로고
    • A. Arcadi, Chem. Rev. 2008, 108, 3266-3325.
    • (2008) Chem. Rev , vol.108 , pp. 3266-3325
    • Arcadi, A.1
  • 19
    • 40949091926 scopus 로고    scopus 로고
    • H. S. Shen, Tetrahedron 2008, 64, 3885-3903;
    • (2008) Tetrahedron , vol.64 , pp. 3885-3903
    • Shen, H.S.1
  • 22
  • 23
    • 33344468391 scopus 로고    scopus 로고
    • I-catalyzed tandem [3, 3]-sigmatropic rearrangement /formal Saito-Myers cyclization of propargyl esters to form aromatic ketones, see
    • I-catalyzed tandem [3, 3]-sigmatropic rearrangement /formal Saito-Myers cyclization of propargyl esters to form aromatic ketones, see
    • (2006) Synlett , pp. 411-414
    • Shibata, T.1    Ueno, Y.2    Kanda, K.3
  • 26
    • 34250806562 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 2610-2612.
    • (2007) Angew. Chem. Int. Ed , vol.46 , pp. 2610-2612
  • 28
    • 70349955169 scopus 로고    scopus 로고
    • Compound 4a is, in fact, a 5-substituted salicylic ester; this subunit, which is quite difficult to prepare because of steric hindrance, is present in several natural products and synthethic compounds with relevant biological activity:
    • Compound 4a is, in fact, a 5-substituted salicylic ester; this subunit, which is quite difficult to prepare because of steric hindrance, is present in several natural products and synthethic compounds with relevant biological activity:
  • 30
    • 17044384198 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 1696-1699;
    • (2005) Angew. Chem. Int. Ed , vol.44 , pp. 1696-1699
  • 32
    • 70349961929 scopus 로고    scopus 로고
    • In particular, (2E, 4Z) -6-methoxycarbonyl-5-phenyl-2, 4-hexadienoic acid (5), which results from the formal hydration of 2a, was isolated (81%) when the reaction was performed in MeOH.
    • In particular, (2E, 4Z) -6-methoxycarbonyl-5-phenyl-2, 4-hexadienoic acid (5), which results from the formal hydration of 2a, was isolated (81%) when the reaction was performed in MeOH.
  • 33
    • 70349936633 scopus 로고    scopus 로고
    • See the Supporting Information
    • See the Supporting Information.
  • 34
    • 70349949305 scopus 로고    scopus 로고
    • The effects of ligands in homogeneous gold catalysis has been recently revised, see
    • The effects of ligands in homogeneous gold catalysis has been recently revised, see
  • 37
    • 67749091068 scopus 로고    scopus 로고
    • The gold-catalyzed hydration of a triple bond has been recently reported with as low as 10 ppm catalyst loading: N Marion, R. S. Ramon, S. P. Nolan, J. Am. Chem. Soc. 2009, 131, 448-449.
    • The gold-catalyzed hydration of a triple bond has been recently reported with as low as 10 ppm catalyst loading: N Marion, R. S. Ramon, S. P. Nolan, J. Am. Chem. Soc. 2009, 131, 448-449.
  • 38
    • 37249012791 scopus 로고    scopus 로고
    • For example, the gold-catalyzed intramolecular carbocyclization of alkynyl ketones requires heating at 100°8C with a 2-5 mol% catalyst loading: T Jin, Y Yamamoto, Org. Lett. 2007, 9, 5259-5262;
    • a) For example, the gold-catalyzed intramolecular carbocyclization of alkynyl ketones requires heating at 100°8C with a 2-5 mol% catalyst loading: T Jin, Y Yamamoto, Org. Lett. 2007, 9, 5259-5262;
  • 39
    • 56949099150 scopus 로고    scopus 로고
    • when 1,3-enynyl carbonyl compounds are employed, a gold-catalyzed tandem heteroenyne metathesis and Nazarov reaction takes place at 50-1008°C: T Jin, Y. Yamamoto, Org. Lett. 2008, 10, 3137-3139.
    • when 1,3-enynyl carbonyl compounds are employed, a gold-catalyzed tandem heteroenyne metathesis and Nazarov reaction takes place at 50-1008°C: T Jin, Y. Yamamoto, Org. Lett. 2008, 10, 3137-3139.
  • 40
    • 33644949668 scopus 로고    scopus 로고
    • The regioselectivity depends on the substitution pattern of the triple bond for the intramolecular gold-catalyzed cycloisomerization of acetylenic carboxylic acids: E. Genin, P. Y. Toullec, S. Antoniotti, C Brancour, J.-P. Genêt, V. Michelet, J. Am. Chem. Soc. 2006, 128, 3112-3113
    • The regioselectivity depends on the substitution pattern of the triple bond for the intramolecular gold-catalyzed cycloisomerization of acetylenic carboxylic acids: E. Genin, P. Y. Toullec, S. Antoniotti, C Brancour, J.-P. Genêt, V. Michelet, J. Am. Chem. Soc. 2006, 128, 3112-3113.
  • 41
    • 70349955172 scopus 로고    scopus 로고
    • For an interesting discussion regarding the nature of intermediates in gold-catalyzed reactions, see
    • For an interesting discussion regarding the nature of intermediates in gold-catalyzed reactions, see
  • 43
    • 53249152128 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 6754-6756;
    • (2008) Angew. Chem. Int. Ed , vol.47 , pp. 6754-6756
  • 45
    • 53049098944 scopus 로고    scopus 로고
    • for a mechanistic perspective review on gold-catalyzed cycloisomerizations of enynes, see
    • Angew. Chem. Int. Ed. 2008, 47, 5030-5033; for a mechanistic perspective review on gold-catalyzed cycloisomerizations of enynes, see
    • (2008) Angew. Chem. Int. Ed , vol.47 , pp. 5030-5033
  • 47
    • 70349963203 scopus 로고    scopus 로고
    • Alternatively, a 6π electrocyclization through mesomeric intermediate IIIb may take place to give IV.
    • Alternatively, a 6π electrocyclization through mesomeric intermediate IIIb may take place to give IV.
  • 48
    • 70349950870 scopus 로고    scopus 로고
    • 13C shifts of the |3-alkyne carbon atom in the NMR spectra of compounds 2 (δ = 33.9-39.5 ppm) versus 6a-d (δ = 84.3-87.3 ppm) and 6e (δ = 85.8 ppm).
    • 13C shifts of the |3-alkyne carbon atom in the NMR spectra of compounds 2 (δ = 33.9-39.5 ppm) versus 6a-d (δ = 84.3-87.3 ppm) and 6e (δ = 85.8 ppm).
  • 49
    • 34848858217 scopus 로고    scopus 로고
    • (M.) Hii
    • and references therein. For general methodologies for the synthesis of unsymmetrical terphenyls, see
    • For general methodologies for the synthesis of unsymmetrical terphenyls, see J. M. Antelo Míguez, L. A. Adrio, A. Sousa-Pedrares, J. M. Vila, K. K. (M.) Hii, J. Org. Chem. 2007, 72, 7771-7774, and references therein.
    • (2007) J. Org. Chem , vol.72 , pp. 7771-7774
    • Antelo, J.M.1    Míguez, L.A.2    Adrio, A.3    Sousa-Pedrares, J.M.4    Vila, K.K.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.