The Role of Reversible Oxidative Addition in Selective Palladium(0)-Catalyzed Intramolecular Cross-Couplings of Polyhalogenated Substrates: Synthesis of Brominated Indoles
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- 作者：Stephen G. Newman ; Mark Lautens
- 刊名：Journal of the American Chemical Society
- 出版年：2010
- 出版时间：August 25, 2010
- 年：2010
- 卷：132
- 期：33
- 页码：11416-11417
- 全文大小：174K
- 年卷期：v.132,no.33(August 25, 2010)
- ISSN：1520-5126
文摘
A Pd(0)-catalyzed C−N bond-forming reaction leading to the synthesis of brominated indoles is described. The use of the phosphine ligand PtBu3 is necessary for reactivity. It is proposed that the bulky ligand serves to prevent inhibition of the catalyst by facilitating reversible oxidative addition into the product C−Br bond. Intramolecular coupling of a vinyl bromide in the presence of an aryl iodide can take place, demonstrating unprecedented levels of selectivity.