CRCU

Chemical Research in Chinese Universities ›› 2013, Vol. 29 ›› Issue (4): 678-681.doi: 10.1007/s40242-013-3057-z

• Articles • Previous Articles     Next Articles

Stereoselective Palladium-catalyzed Cross-coupling of (2-Amido-1-phenylpropyl)zinc Compounds with Aryl Bromides

TANG Shi1,2, ZHOU Dong1, LI Shu-hua1, WANG Nai-xing2   

  1. 1. College of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, P. R. China;
    2. Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. China
  • Received:2013-01-31 Revised:2013-03-01 Online:2013-08-01 Published:2013-07-15
  • Contact: TANG Shi E-mail:shitang@126.com
  • Supported by:

    Supported by the National Natural Science Foundation of China(No.21172227) and the Research-based Learning and Innovative Experiment Project of Jishou University, China (No.JSU-CX-2013-03).

Cited

2

Abstract:

A controllable diastereoselective C(sp2)―C(sp3) Negishi coupling reaction of secondary benzylic zinc reagents with aryl bromides to form medicinally important 2-arylphenylethylamines was demonstrated. In the presence of Pd(OAc)2 and 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl(S-phos), open-chain(2-amido-1-phenylethyl)zinc reagent bearing a β-NHAc or NHCHO group undergoes coupling reaction to give syn-1-arylphenylethylamine mainly, whereas the zinc reagent bearing a sterically hindered β-amido group, for example NHCOC(CH3)2OTBS undergoes the coupling reaction to yield anti-1-arylphenylethylamines with a configuration inversion. In addition, a working mechanism for the stereoselective Negishi cross-coupling was also proposed.

Key words: Palladium, Stereoselective, Negishi coupling, Benzylic zinc, 2-Arylphenylethylamine