4.8 Article

Solvent-Controlled Switchable C-H Alkenylation of 4-Aryl-1H-pyrrole-3-carboxylates: Application to the Total Synthesis of (±)-Rhazinilam

Journal

ORGANIC LETTERS
Volume 16, Issue 18, Pages 4884-4887

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol5023933

Keywords

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Funding

  1. NSFC [21272276]
  2. SKLNM [JKGZ201110, ZZJQ201306]
  3. Ministry of Education of China [PSCIRT-1193]

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A solvent-controlled switchable C-H alkenylation of 4-aryl-1H-pyrrole-3-carboxylates via a Pd(OAc)(2) catalyzed oxidative Heck reaction was first realized. The corresponding C2 and C5 alkenylation products were obtained in good yields with high regioselectivities, respectively. The selective C5-alkenylation was successfully applied to the total synthesis of (+/-)-rhazinilam.

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