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Volumn 130, Issue 34, 2008, Pages 11300-11302

Pd-catalyzed direct arylation of tautomerizable heterocycles with aryl boronic acids via C-OH bond activation using phosphonium salts

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; HETEROCYCLIC COMPOUND; PALLADIUM; PHOSPHONIUM DERIVATIVE;

EID: 50249166697     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja804804p     Document Type: Article
Times cited : (114)

References (61)
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    • For recent reviews, see: a
    • For recent reviews, see: (a) Godula, K.; Sames, D. Science 2006, 312, 67.
    • (2006) Science , vol.312 , pp. 67
    • Godula, K.1    Sames, D.2
  • 12
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    • For direct arylations of aryl methyl ethers and direct alkylations of benzyl methyl ethers via C-OMe bond activation, see: (a) Kakiuchi, F, Usui, M, Ueno, S, Chatani, N, Murai, S. J. Am. Chem. Soc. 2004, 126, 2706
    • For direct arylations of aryl methyl ethers and direct alkylations of benzyl methyl ethers via C-OMe bond activation, see: (a) Kakiuchi, F.; Usui, M.; Ueno, S.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 2004, 126, 2706.
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    • Kang, F.-A.; Murray, W. V. Abstracts of Papers, 228th National Meeting of the American Chemical Society, Philadelphia, PA, August, 2004; American Chemical Society: Washington, DC, 2004; ORGN-702.
    • (a) Kang, F.-A.; Murray, W. V. Abstracts of Papers, 228th National Meeting of the American Chemical Society, Philadelphia, PA, August, 2004; American Chemical Society: Washington, DC, 2004; ORGN-702.
  • 20
    • 50249171297 scopus 로고    scopus 로고
    • For conventional non-chemoselective halo-de-hydroxylation conditions involving phosphonium intermediates generated in situ using halogenation reagents, such as NBS/CX4-P(NMe2)3, or I 2-PPh3, see: (a) Smith, M. B, March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 5th ed, John Wiley & Sons: New York, 2001; p 518
    • 3, see: (a) Smith, M. B.; March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 5th ed.; John Wiley & Sons: New York, 2001; p 518.
  • 24
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    • Since the manufacture and utilization of BroP and BOP involve the use and formation of the carcinogenic HMPA, the unpopular BroP and BOP have been replaced by their environmentally benign analogues, i.e, PyBroP and PyBOP, as the newer generation of phosphonium reagents, see: (a) Coste, J, Le-Nguyen, D, Castro, B. Tetrahedron Lett. 1990, 31, 205
    • Since the manufacture and utilization of BroP and BOP involve the use and formation of the carcinogenic HMPA, the unpopular BroP and BOP have been replaced by their environmentally benign analogues, i.e., PyBroP and PyBOP, as the newer generation of phosphonium reagents, see: (a) Coste, J.; Le-Nguyen, D.; Castro, B. Tetrahedron Lett. 1990, 31, 205.
  • 25
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    • Therefore, in terms of environmental impact, atom-economy, and reactivity, the order of the preferred phosphonium reagents for coupling reactions should be: PyBroP > PyBOP ≫ BroP > BOP
    • (b) Coste, J.; Frerot, E.; Jouin, P.; Castro, B. Tetrahedron Lett. 1991, 32, 1967. Therefore, in terms of environmental impact, atom-economy, and reactivity, the order of the preferred phosphonium reagents for coupling reactions should be: PyBroP > PyBOP ≫ BroP > BOP.
    • (1991) Tetrahedron Lett , vol.32 , pp. 1967
    • Coste, J.1    Frerot, E.2    Jouin, P.3    Castro, B.4
  • 26
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    • For recent applications of the phosphonium coupling methodology to the C-N bond formations (listed chronologically by their submission or filling dates), see: (a) Wan, Z.-K.; Binnum, E.; Wilson, D. P.; Lee, J. Org. Lett. 2005, 7, 5877.
    • For recent applications of the phosphonium coupling methodology to the C-N bond formations (listed chronologically by their submission or filling dates), see: (a) Wan, Z.-K.; Binnum, E.; Wilson, D. P.; Lee, J. Org. Lett. 2005, 7, 5877.
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    • Interestingly, direct arylation of the multifunctionalized 2-pyrimidinone with aryl boronic acids produced the unexpected biaryl ethers (9a and 10a, C-O bond formation) as the minor side products along with the desired biaryl products (9 and 10, To confirm their structures, the identical biaryl ethers 9a and 10a were alternatively prepared via our previous phosphonium coupling for the direct C-O bond formation by using the corresponding phenols (see Supporting Information, The reason for the biaryl ether formation on this substrate was unclear, and neither C-C nor C-O bond formation was observed in the absence of PyBroP. For recent reviews on biaryl ether synthesis via Cu-mediated C-O bond formation using aryl boronic acids, see: (a) Ley, S. L, Thomas, A. W. Angew. Chem, Int. Ed. 2003, 42, 5400
    • Interestingly, direct arylation of the multifunctionalized 2-pyrimidinone with aryl boronic acids produced the unexpected biaryl ethers (9a and 10a) (C-O bond formation) as the minor side products along with the desired biaryl products (9 and 10). To confirm their structures, the identical biaryl ethers 9a and 10a were alternatively prepared via our previous phosphonium coupling for the direct C-O bond formation by using the corresponding phenols (see Supporting Information). The reason for the biaryl ether formation on this substrate was unclear, and neither C-C nor C-O bond formation was observed in the absence of PyBroP. For recent reviews on biaryl ether synthesis via Cu-mediated C-O bond formation using aryl boronic acids, see: (a) Ley, S. L.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.