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

Džambaski, Zdravko; Bondžić, Bojan

doi:10.1039/C9OB01090D

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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)

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

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	11
	6

TY  - 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 . .