Synthesis of Carbolines via Palladium/Carboxylic Acid Joint Catalysis

被引：34

作者：

Cera, Gianpiero ^{[1
]}

Lanzi, Matteo ^{[1
]}

Balestri, Davide ^{[1
]}

Della Ca, Nicola ^{[1
]}

Maggi, Raimondo ^{[1
]}

Bigi, Franca ^{[1
,3
]}

Malacria, Max ^{[2
]}

Maestri, Giovanni ^{[1
]}

机构：

[1] Univ Parma, Dipartimento Sci Chim Vita & Sostenibilita Ambien, Parco Area Sci 17-A, I-43124 Parma, Italy

[2] UPMC Sorbonne Univ, IPCM UMR CNRS 8232, 4 Pl Jussieu,C 229, F-75005 Paris, France

[3] IMEM CNR, Parco Area Sci 37-A, I-43124 Parma, Italy

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 11期

关键词：

TETRAHYDRO-BETA-CARBOLINES; PICTET-SPENGLER REACTION; C-H ACTIVATION; ENANTIOSELECTIVE SYNTHESIS; ALLYLIC ALKYLATION; INDOLES; ALKYNES; ALLYLATION; AMINES; CYCLIZATION;

D O I：

10.1021/acs.orglett.8b01072

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The combination of a Pd(0) complex with benzoic acid converts propargylic tryptamines to the corresponding tetrahydro-beta-carbolines. The method uses unprotected indoles and affords the desired products with ample functional group tolerance. Detailed modeling studies reveal a close synergy between the organic and metal catalysts, which enables sequential alkyne isomerization, indole C-H activation, and eventual C-C reductive elimination to afford the target heterocycles.

引用

收藏

页码：3220 / 3224

页数：5

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