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Dehydrogenative C(sp3)–H bond functionalization of tetrahydroisoquinolines mediated by organic oxidants under mild conditions

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2019
Authors
Džambaski, Zdravko
Bondžić, Bojan
Article (Published version)
,
Royal Society of Chemistry
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Abstract
The organocatalyzed Mannich reaction of unsubstituted and N-aryl-substituted tetrahydroisoquinolines (THIQs) and the Strecker reaction of several N-aryl-substituted THIQs through dehydrogenative C(sp3)–H bond functionalization (cross-dehydrogenative coupling) promoted by organic single electron oxidants DDQ and IBX are presented. The C–H oxidation/Mannich reaction of less reactive N-aryl substituted pyrrolidines is achieved via metal catalyzed photoredox catalysis. Operationally simple procedures provide desired products in an effective and time preserving manner.
Keywords:
Cross-dehydrogenative coupling / Mannich reaction
Source:
Organic & Biomolecular Chemistry, 2019, 17, 26, 6420-6425
Publisher:
  • Royal Society of Chemistry (RSC)
Projects:
  • Experimental and theoretical study of reactivity and biological activity of stereodefined thiazolidines and their synthetic analogues (RS-172020)
  • COST action CA15106: C–H Activation in Organic Synthesis (CHAOS)

DOI: 10.1039/C9OB01090D

ISSN: 1477-0520; 1477-0539

PubMed: 31225575

WoS: 000474089200014

Scopus: 2-s2.0-85068414427
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URI
http://cer.ihtm.bg.ac.rs/handle/123456789/3063
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