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Volumn 76, Issue 6, 2011, Pages 1949-1952

Rh-catalyzed carbonylation of arylzinc compounds yielding symmetrical diaryl ketones by the assistance of oxidizing agents

Author keywords

[No Author keywords available]

Indexed keywords

ARYL LIGANDS; ARYLZINC COMPOUNDS; BIARYLS; DIARYL KETONES; GOOD YIELD; HOMOCOUPLING; NI CATALYSTS; OXIDATIVE HOMOCOUPLING; OXIDIZING AGENTS;

EID: 79953902479     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1025173     Document Type: Article
Times cited : (31)

References (70)
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    • Synthesis of natural products via palladium-catalyzed carbonylation
    • Negishi, E., Ed.; Wiley-Interscience: New York
    • (a) Mori, M. Synthesis of Natural Products via Palladium-Catalyzed Carbonylation. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002; Vol. II, pp 2663-2682.
    • (2002) Handbook of Organopalladium Chemistry for Organic Synthesis , vol.2 , pp. 2663-2682
    • Mori, M.1
  • 6
    • 33947305793 scopus 로고
    • For Pd-catalyzed carbonylation of ArHgCl or Ar4Sn with CuX2 as oxidizing agent, yielding symmetrical diaryl ketones in low to moderate yields, see: (a) Heck, R. F. J. Am. Chem. Soc. 1968, 90, 5546-5548.
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 5546-5548
    • Heck, R.F.1
  • 7
    • 0034865196 scopus 로고    scopus 로고
    • (b) Ohe, T.; Motofusa, S.; Ohe, K.; Uemura, S. Bull. Chem. Soc. Jpn. 2001, 74, 1343-1348. For Pd-catalyzed carbonylation of alkylzinc iodide with allyl benzoate or O2 as oxidizing agent, see
    • (2001) Bull. Chem. Soc. Jpn. , vol.74 , pp. 1343-1348
    • Ohe, T.1    Motofusa, S.2    Ohe, K.3    Uemura, S.4
  • 10
    • 2242424605 scopus 로고
    • For Pd-catalyzed carbonylation of Ar2I+ with Zn or In as reducing agent, yielding symmetrical diaryl ketones, see: (a) Uchiyama, M.; Suzuki, T.; Yamazaki, Y. Chem. Lett. 1983, 1201-1202.
    • (1983) Chem. Lett. , pp. 1201-1202
    • Uchiyama, M.1    Suzuki, T.2    Yamazaki, Y.3
  • 12
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    • (c) Brunet, J.-J.; Zaizi, A. E. J. Organomet. Chem. 1995, 486, 275-277. For Co2(CO)8-mediated carbonylation of iodoarenes, yielding symmetrical diaryl ketones, see
    • (1995) J. Organomet. Chem. , vol.486 , pp. 275-277
    • Brunet, J.-J.1    Zaizi, A.E.2
  • 42
    • 0028886752 scopus 로고
    • For Co-mediated carbonylative homocoupling of arylzinc compounds yielding symmetrical diaryl ketones
    • For Co-mediated carbonylative homocoupling of arylzinc compounds yielding symmetrical diaryl ketones, see: Devasagayaraj, A.; Knochel, P. Tetrahedron Lett. 1995, 36, 8411-8414.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 8411-8414
    • Devasagayaraj, A.1    Knochel, P.2
  • 55
    • 0000789560 scopus 로고
    • note
    • Another synthetic method of symmetrical diaryl ketones from Ar-m (m = Hg,3a,16a Bi, 16b Sn, 3b Pb, 16c or B16d,16e) and CO without oxidants is known, where Ar-m oxidatively adds to catalysts. Comparedto the harshness of the conditions, 3a,16a toxicity,3a,3b16a16c and/or availability3a3b16a-16e of starting materials in comparison with m = Zn, and the low to moderate yields of products reported, 3a3b16b,16d,16e our method is far more useful.(a) Larock, R. C.; Hershberger, S. A. J. Org. Chem. 1980, 45, 3840-3846.
    • (1980) J. Org. Chem. , vol.45 , pp. 3840-3846
    • Larock, R.C.1    Hershberger, S.A.2
  • 67
    • 53849139127 scopus 로고    scopus 로고
    • Under conditions similar to those of runs 1-5, functionalized 1, e.g., 1c or 1f, took part in the reaction to yield the corresponding biaryls in 82% or 97% yields, respectively. Recently, Rh-catalyzed oxidative homocoupling of arylmetallic nucleophiles was reported for the first time, using arylboronic acids and 2,2,6,6-tetramethylpiperidine-N-oxyl radical as the nucleophile and oxidant, respectively. See: Vogler, T.; Studer, A. Adv. Synth. Catal. 2008, 350, 1963-1967.
    • (2008) Adv. Synth. Catal. , vol.350 , pp. 1963-1967
    • Vogler, T.1    Studer, A.2
  • 68
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    • In the reaction solution of runs 1-7, 3a was not detected
    • In the reaction solution of runs 1-7, 3a was not detected.
  • 69
    • 84890738094 scopus 로고    scopus 로고
    • note
    • 2Ni(CO), 0.543; CH3Rh(CO); 0.382.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.