Activation of Primary Amines by Copper(I)-Based Lewis Acid Promoters in the Solventless Synthesis of Secondary Propargylamines

被引：6

作者：

Cimarelli, Cristina ^{[1
]}

Navazio, Federica ^{[1
]}

Rossi, Federico V. ^{[1
]}

Del Bello, Fabio ^{[2
]}

Marcantoni, Enrico ^{[1
]}

机构：

[1] Univ Camerino, Sch Sci & Technol, Div Chem, Via S Agostino 1, I-62032 Camerino, Italy

[2] Univ Camerino, Sch Pharm, Med Chem Unit, Via S Agostino 1, I-62032 Camerino, Italy

来源：

SYNTHESIS-STUTTGART | 2019年 / 51卷 / 11期

关键词：

propargylamines; A (3) -coupling; primary amines; copper; cerium trichloride; Lewis acids; C-H ACTIVATION; CATALYZED CYCLOISOMERIZATIONS; CARBON-DIOXIDE; 2-OXAZOLIDINONES; ROUTE; GOLD; CO2; CYCLIZATION; ADDITIONS; SYSTEM;

D O I：

10.1055/s-0037-1612253

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Primary amines are activated by copper(I)-based Lewis acid promoters in an A (3) -coupling one-pot solventless reaction with aldehydes and phenylacetylene for the synthesis of secondary propargylamines. The reaction is promoted by a CuSO (4) /NaI system, a practical precursor of the in situ generated effective CuI/I (2) system, that worked well, but only in a restricted number of examples. Substitution of I (2) with CeCl (3) 7H (2) O in a one-pot two-step reaction provided good yields and a wider applicability, with the added value given by a safer procedure.

引用

页码：2387 / 2396

页数：10

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