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钯-锡杂化双金属催化:Suzuki 串联环封闭序列合成茚并[2,1-b]噻吩和茚并[2,1-b]吲哚。

Heterobimetallic Pd-Sn catalysis: a Suzuki, tandem ring-closing sequence toward indeno[2,1-b]thiophenes and indeno[2,1-b]indoles.

机构信息

Organometallics & Catalysis Laboratory, Department of Chemistry, Indian Institute of Technology, Kharagpur 721302, India.

出版信息

Org Lett. 2012 Sep 21;14(18):4870-3. doi: 10.1021/ol3021995. Epub 2012 Aug 31.

DOI:10.1021/ol3021995
PMID:22937993
Abstract

Indeno[2,1-b]thiophene and indeno[1,2-b]indole motifs have been obtained in moderate to good yields from easily available substituted boronic acids, 2-bromo aryl/vinyl aldehydes, and nucleophiles such as arenes/heteroarenes and others using a catalytic combination of bimetallic "Pd-Sn" and AgPF(6). This formal three-component coupling involves a Suzuki reaction followed by nucleophile assisted tandem ring closure. The sequential synthesis of substituted heterocycle-fused indenes, benzofluorene, and fluorenes was also accomplished.

摘要

从易得的取代硼酸、2-溴代芳基/乙烯基醛以及亲核试剂(如芳基/杂芳基等)出发,通过双金属“Pd-Sn”和 AgPF(6)的催化组合,以中等至良好的产率得到了吲哚并[2,1-b]噻吩和吲哚并[1,2-b]吲哚母核。该形式的三组分偶联反应涉及Suzuki 反应,随后是亲核试剂辅助的串联环化。还完成了取代杂环稠合茚、苯并芴和芴的连续合成。

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