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

Royal Society of Chemistry
Metadata
Show full item recordAbstract
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)
Funding / 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
Collections
Institution/Community
IHTMTY - JOUR AU - Džambaski, Zdravko AU - Bondžić, Bojan PY - 2019 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/3063 AB - 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. PB - Royal Society of Chemistry (RSC) T2 - Organic & Biomolecular Chemistry T1 - Dehydrogenative C(sp3)–H bond functionalization of tetrahydroisoquinolines mediated by organic oxidants under mild conditions VL - 17 IS - 26 SP - 6420 EP - 6425 DO - 10.1039/C9OB01090D ER -
@article{ author = "Džambaski, Zdravko and Bondžić, Bojan", year = "2019", 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.", publisher = "Royal Society of Chemistry (RSC)", journal = "Organic & Biomolecular Chemistry", title = "Dehydrogenative C(sp3)–H bond functionalization of tetrahydroisoquinolines mediated by organic oxidants under mild conditions", volume = "17", number = "26", pages = "6420-6425", doi = "10.1039/C9OB01090D" }
Džambaski, Z.,& Bondžić, B.. (2019). Dehydrogenative C(sp3)–H bond functionalization of tetrahydroisoquinolines mediated by organic oxidants under mild conditions. in Organic & Biomolecular Chemistry Royal Society of Chemistry (RSC)., 17(26), 6420-6425. https://doi.org/10.1039/C9OB01090D
Džambaski Z, Bondžić B. Dehydrogenative C(sp3)–H bond functionalization of tetrahydroisoquinolines mediated by organic oxidants under mild conditions. in Organic & Biomolecular Chemistry. 2019;17(26):6420-6425. doi:10.1039/C9OB01090D .
Džambaski, Zdravko, Bondžić, Bojan, "Dehydrogenative C(sp3)–H bond functionalization of tetrahydroisoquinolines mediated by organic oxidants under mild conditions" in Organic & Biomolecular Chemistry, 17, no. 26 (2019):6420-6425, https://doi.org/10.1039/C9OB01090D . .