Synthesis of Pyrrolidines and Pyrroles via Tandem Amination/Cyanation/Alkylation and Amination/Oxidation Sequences.

Synthesis of Pyrrolidines and Pyrroles via Tandem Amination/Cyanation/Alkylation and Amination/Oxidation Sequences.
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DOI:
10.1002/ejoc.201402748
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发表时间:
2014-09-01
影响因子:
2.8
通讯作者:
Xu, Bo
Xu, Bo
中科院分区:
化学3区
文献类型:
--
作者:
Han, Junbin;Lu, Zhichao;Hammond, Gerald B.;Xu, Bo

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以伯胺连接的炔1为原料,采用铜催化的三组分串联胺化/氰化/烷基化反应,以良好的产率和区域选择性合成了α-CN吡咯烷6。此外,银介导的仲胺系链的炔7的串联胺化/氧化以良好的产率产生官能化的吡咯8。所有反应在一锅中进行,没有任何保护/脱保护步骤。
Starting from a primary amine-tethered alkyne 1, a copper-catalyzed three-component tandem amination/cyanation/alkylation sequence gives α-CN pyrrolidine 6 in good yield and regioselectivity. Also, a silver mediated tandem amination/oxidation of a secondary amine-tethered alkyne 7 produces functionalized pyrrole 8 in good yield. All reactions were conducted in one pot without any protection/deprotection steps.
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