Dehydrogenative C(sp3)–H bond functionalization of tetrahydroisoquinolines mediated by organic oxidants under mild conditions
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2019
Article (Published version)

Royal Society of Chemistry
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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 reactionSource:
Organic & Biomolecular Chemistry, 2019, 17, 26, 6420-6425Publisher:
- 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