Highly ortho-selective cross-coupling of dichlorobenzene derivatives with grignard reagents

Organic Letters

Volumn 9, Issue 26, 2007, Pages 5593-5595

  Ishikawa, Shunpei ^a   Manabe, Kei ^a  

^a RIKEN   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 38349102530     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702646s     Document Type: Article

References (34)

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20. Electron-withdrawn groups such as nitro and carboxylato groups are known to facilitate cros- coupling at the ortho-position. This effect has been attributed to coordination of these groups to Pd in the oxidative addition of the o-C-X bond: (a) Kim, Y. M.; Yu, S. J. Am. Chem. Soc. 2003, 125, 1696.
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26. See also: (b) Sinclair, D. J.; Sherburn, M. S. J. Org. Chem. 2005, 70, 3730.
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28. 3 (4.8 mol%), and KF (3 equiv) in THF at 70°C for 21 h gave ortho (32%), isomer (14%), and di (12%). For Suzuki-Miyaura coupling using these conditions, see: Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020.
29. Examples of cross-coupling of halophenols with Grignard reagents: (a) Jendralla, H.; Chen, L.-J. Synthesis 1990, 827.
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33. Activation of C-X bonds by coordination to Mg was reported by Nakamura et al. in their Ni-catalyzed cross coupling of ArF or ArCl with Grignard reagents: Yoshikai, N.; Mashima, H.; Nakamura, E. J. Am. Chem. Soc. 2005, 127, 17978.
34. Nakamura et al. also used a phosphine with a hydroxy group for Ni-catalyzed cross-coupling. See ref. 13.