Synthesis of 4-Alkylidene-Substituted 1,2,3,4-Tetrahydroisoquinolines via Palladium-Catalyzed Carbopalladation/C–H Activation of 2-Bromobenzyl-N-propargylamines

Kanagaraj Naveen; Avanashiappan Nandakumar; Paramasivan Thirumalai Perumal

doi:10.1055/s-0034-1380414

Synthesis, Inhaltsverzeichnis

Synthesis 2015; 47(11): 1633-1642
DOI: 10.1055/s-0034-1380414

paper

Synthesis of 4-Alkylidene-Substituted 1,2,3,4-Tetrahydroisoquinolines via Palladium-Catalyzed Carbopalladation/C–H Activation of 2-Bromobenzyl-N-propargylamines

Kanagaraj Naveen

Organic Chemistry Division, CSIR-Central Leather Research Institute, Adyar, Chennai-600 020, India eMail: ptperumal@gmail.com

,

Avanashiappan Nandakumar

Organic Chemistry Division, CSIR-Central Leather Research Institute, Adyar, Chennai-600 020, India eMail: ptperumal@gmail.com

,

Paramasivan Thirumalai Perumal*

Organic Chemistry Division, CSIR-Central Leather Research Institute, Adyar, Chennai-600 020, India eMail: ptperumal@gmail.com

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Abstract

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Abstract

Tetrasubstituted alkene-based 1,2,3,4-tetrahydroisoquinolines are synthesized via the formation of a cyclic carbopalladation complex followed by C–H bond activation of the sp² carbon in arenes. This domino reaction proceeds with good selectivity and provides good yields of the products. The requisite starting materials are synthesized by copper(I) iodide catalyzed A³-coupling reactions.

Key words

palladium - C–H activation - alkynes - heterocycles - carbopalladation

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Referenzen

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