Synthesis of Trisubstituted Pyrroles from Rhodium-Catalyzed Alkyne Head-to-Tail Dimerization and Subsequent Gold-Catalyzed Cyclization
Synthesis of Trisubstituted Pyrroles from Rhodium-Catalyzed Alkyne Head-to-Tail Dimerization and Subsequent Gold-Catalyzed Cyclization
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DOI：
10.1002/adsc.200800735
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发表时间：
2009-06-01
影响因子：
5.4
通讯作者：
Li, Xingwei
中科院分区：
文献类型：
--
作者：
Peng, Hong Mei;Zhao, Jing;Li, Xingwei
在温和的条件下，用铑催化剂高选择性地实现了N-保护的炔丙胺在一种相当罕见的头-尾模式下的二聚。N-保护基可以是磺酰基、氨基甲酸酯或羰基官能团，并且（环辛烷）氯化铑二聚体/1，1 ′-双（二苯基膦基）二茂铁{[Rh（COD）Cl]（2）/dppf}以及三（三苯基膦）氯化铑[Rh（PPh 3）（3）Cl]被证明是活性催化剂。此外，这些功能gem-enynes随后进行选择性的金（III）催化的分子内氢胺化，在温和的条件下得到三取代的吡咯。
Dimerization of N-protected propargylic amines in a rather rare head-to-tail mode has been achieved under mild conditions with high selectivity using rhodium catalysts. The N-protecting group could be a sulfonyl, carbamate, or carbonyl functionality and (cyclooctadiene)rhodium chloride dimer/1,1'-bis(diphenylphosphino)ferrocene {[Rh(COD)Cl](2)/dppf} as well as tris(triphenylphosphine)rhodium chloride [Rh(PPh3)(3)Cl] proved to be active catalysts. In addition, these functionalized gem-enynes subsequently undergo selective gold(III)-catalyzed intramolecular hydroamination to give trisubstituted pyrroles under mild conditions.