Single and double Suzuki-Miyaura couplings with symmetric dihalobenzenes

Journal of Organic Chemistry

Volumn 70, Issue 9, 2005, Pages 3730-3733

  Sinclair, David J ^a   Sherburn, Michael S ^a  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST SELECTIVITY; ELECTRON ENERGY LEVELS; ESTERS; ORGANIC ACIDS; REACTION KINETICS;

ARYLBORONIC ACIDS; COUPLING SELECTIVITY; STERIC HINDERANCE; SUZUKI-MIYAURA COUPLINGS;

AROMATIC HYDROCARBONS;

3 DIBROMOBENZENE; 3 DIIODOBENZENE; 4 DIBROMOBENZENE; 4 DIIODOBENZENE; ARYLBORONIC ACID; BENZENE DERIVATIVE; BORONIC ACID DERIVATIVE; DIHALOBENZENE; ESTER; UNCLASSIFIED DRUG;

ARTICLE; SUZUKI REACTION;

EID: 17744384723     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050105q     Document Type: Article

References (41)

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35. In light of this result, it is interesting to note that of the 37 monocouplings of symmetrical substrates mentioned in ref 3, none were with diiodides.
36. Bromo-4-iodobenzene is 28 times more expensive per mole than 1,4-dibromobenzene, based upon 2004 catalogue prices for 25 and 500 g pack sizes, respectively.
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39. Selective single couplings of 1,3,5-tribromobenzene have been reported: (a) Manabe, K.; Okamura, K.; Date, T.; Koga, K. J. Org. Chem. 1993, 58, 6692-6700. (b) Caneschi, A.; Dei, A.; Mussari, C. P.; Shultz, D. A.; Sorace, L.; Vostrikova, K. E. Inorg. Chem. 2002, 41, 1086-1092. (c) Grilli, S.; Lunazzi, L.; Mazzanti, A.; Pinamonti, M. J. Org. Chem. 2002, 67, 5733-5738.
40. Selective single couplings of 1,3,5-tribromobenzene have been reported: (a) Manabe, K.; Okamura, K.; Date, T.; Koga, K. J. Org. Chem. 1993, 58, 6692-6700. (b) Caneschi, A.; Dei, A.; Mussari, C. P.; Shultz, D. A.; Sorace, L.; Vostrikova, K. E. Inorg. Chem. 2002, 41, 1086-1092. (c) Grilli, S.; Lunazzi, L.; Mazzanti, A.; Pinamonti, M. J. Org. Chem. 2002, 67, 5733-5738.
41. Selective single couplings of 1,3,5-tribromobenzene have been reported: (a) Manabe, K.; Okamura, K.; Date, T.; Koga, K. J. Org. Chem. 1993, 58, 6692-6700. (b) Caneschi, A.; Dei, A.; Mussari, C. P.; Shultz, D. A.; Sorace, L.; Vostrikova, K. E. Inorg. Chem. 2002, 41, 1086-1092. (c) Grilli, S.; Lunazzi, L.; Mazzanti, A.; Pinamonti, M. J. Org. Chem. 2002, 67, 5733-5738.