Issue 39, 2023

Cu(ii)-catalyzed cross coupling cyanomethylation of tetrahydroisoquinolines with α-bromoalkylnitrile

Abstract

Herein, we present a Cu(II)-mediated C–C reaction with α-haloacetonitrile derivatives and aryl tetrahydroisoquinolines via a coupling of C(sp3)–Br and C(sp3)–H bonds, yielding cyanomethylated tetrahydroisoquinolines. The reaction led to the synthesis of a broad variety of tetrahydroisoquinolines, such as electron donating and electron withdrawing and hetero ring groups substituted tetrahydroisoquinolines. This methodology provides cyanomethylated products (with excellent yields (47%–89%)) and valuable insights for the design of versatile biologically active products.

Graphical abstract: Cu(ii)-catalyzed cross coupling cyanomethylation of tetrahydroisoquinolines with α-bromoalkylnitrile

Supplementary files

Article information

Article type
Paper
Submitted
09 Aug 2023
Accepted
14 Sep 2023
First published
14 Sep 2023

New J. Chem., 2023,47, 18173-18177

Cu(II)-catalyzed cross coupling cyanomethylation of tetrahydroisoquinolines with α-bromoalkylnitrile

M. S. Ahmad, R. Qasim, Q. Zhang, B. Zeng, J. Chen, Q. Wang and K. Meguellati, New J. Chem., 2023, 47, 18173 DOI: 10.1039/D3NJ03726F

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