4.5 Article

Rhodium-Catalyzed Direct Alkenylation and Arylation of Arene C-H Bonds via Decarbonylation of Cinnamoyl Chlorides, Cinnamic Anhydrides, and Poly(aroyl) Chlorides

Journal

ORGANOMETALLICS
Volume 29, Issue 4, Pages 1049-1052

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/om900997y

Keywords

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Funding

  1. National Basic Research Program of China [2009CB825300]
  2. National Natural Science Foundation of China [20972157]
  3. Chinese Academy of Sciences [DICP K2009D04]

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Efficient regioselective direct alkenylation of benzo[h]quinoline was realized with cinnamoyl chlorides as the coupling partners via decarbonylation of the chlorides and C-H bond activation by means of [Rh(CO)(2)Cl](2) as the catalyst in refluxing o-oxlene under phosphine-free conditions. For 2-phenylpridine, [Rh(CO)(2)Cl](2) or [Rh(COD)Cl](2) efficiently promoted its direct alkenylation with cinnamic anhydrides. Polyarenes were synthesized from [Rh(COD)Cl](2)-catalyzed decarbonylative poly(arylation) of isophthaloyl dichloride, terephthaloyl dichloride, or benzene-1,3,5,-tricarbonyl chloride with benzo[h] quinoline.

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