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Transition-Metal-Free Arylation of N-Alkyl-tetrahydroisoquinolines under Oxidative Conditions: A Convenient Synthesis of C1-Arylated Tetrahydroisoquinoline Alkaloids

Kamal Nain Singh*, Satinder V. Kessar, Paramjit Singh, Pushpinder Singh, Manjot Kaur, Aanchal Batra

*Department of Chemistry and Centre of Advanced Studies in Chemistry, Panjab University, Chandigarh 160014, India, Email: knspu.ac.in

K. N. Singh, S. V. Kessar, P. Singh, P. Singh, M. Kaur, A. Batra, Synthesis, 2014, 46, 2644-2650.

DOI: 10.1055/s-0034-1378337 (free Supporting Information)


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Abstract

An oxidative C1 arylation of tetrahydroisoquinolines with aryl Grignard reagents is mediated by diethyl azodicarboxylate (DEAD). This C-H activation under metal-free conditions delivers target compounds, including some naturally occurring alkaloids, in good yields.

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Key Words

arylation, tetrahydroisoquinolines, DEAD, C-H activation, alkaloids, metal-free


ID: J66-Y2014