Direct and Efficient C(sp(3))–H Functionalization of N-Acyl/Sulfonyl Tetrahydroisoquinolines (THIQs) With Electron-Rich Nucleophiles via 2,3-Dichloro-5,6-Dicyano-1,4-Benzoquinone (DDQ) Oxidation

A highly efficient metal-free oxidative direct C(sp(3))–H functionalization of N-acyl/sulfonyl 1,2,3,4-tetrahydroisoquinolines (THIQs) with a wide range of electron-rich nucleophiles was accomplished under mild conditions through oxidation with DDQ and subsequent trapping of the resulting reactive a...

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Autores principales: Yu, Heesun, Kim, Hyoungsu, Baek, Seung-Hoon, Lee, Dongjoo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2020
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7403605/
https://www.ncbi.nlm.nih.gov/pubmed/32850649
http://dx.doi.org/10.3389/fchem.2020.00629
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author Yu, Heesun
Kim, Hyoungsu
Baek, Seung-Hoon
Lee, Dongjoo
author_facet Yu, Heesun
Kim, Hyoungsu
Baek, Seung-Hoon
Lee, Dongjoo
author_sort Yu, Heesun
collection PubMed
description A highly efficient metal-free oxidative direct C(sp(3))–H functionalization of N-acyl/sulfonyl 1,2,3,4-tetrahydroisoquinolines (THIQs) with a wide range of electron-rich nucleophiles was accomplished under mild conditions through oxidation with DDQ and subsequent trapping of the resulting reactive and stable N-acyl/sulfonyl iminium ions. The synthetic utility of this method was illustrated by a concise and efficient total synthesis of (±)-benzo[a]quinolizidine (10) in 3 steps from the known N-Cbz 1,2,3,4-THIQ 4b.
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spelling pubmed-74036052020-08-25 Direct and Efficient C(sp(3))–H Functionalization of N-Acyl/Sulfonyl Tetrahydroisoquinolines (THIQs) With Electron-Rich Nucleophiles via 2,3-Dichloro-5,6-Dicyano-1,4-Benzoquinone (DDQ) Oxidation Yu, Heesun Kim, Hyoungsu Baek, Seung-Hoon Lee, Dongjoo Front Chem Chemistry A highly efficient metal-free oxidative direct C(sp(3))–H functionalization of N-acyl/sulfonyl 1,2,3,4-tetrahydroisoquinolines (THIQs) with a wide range of electron-rich nucleophiles was accomplished under mild conditions through oxidation with DDQ and subsequent trapping of the resulting reactive and stable N-acyl/sulfonyl iminium ions. The synthetic utility of this method was illustrated by a concise and efficient total synthesis of (±)-benzo[a]quinolizidine (10) in 3 steps from the known N-Cbz 1,2,3,4-THIQ 4b. Frontiers Media S.A. 2020-07-29 /pmc/articles/PMC7403605/ /pubmed/32850649 http://dx.doi.org/10.3389/fchem.2020.00629 Text en Copyright © 2020 Yu, Kim, Baek and Lee. http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
spellingShingle Chemistry
Yu, Heesun
Kim, Hyoungsu
Baek, Seung-Hoon
Lee, Dongjoo
Direct and Efficient C(sp(3))–H Functionalization of N-Acyl/Sulfonyl Tetrahydroisoquinolines (THIQs) With Electron-Rich Nucleophiles via 2,3-Dichloro-5,6-Dicyano-1,4-Benzoquinone (DDQ) Oxidation
title Direct and Efficient C(sp(3))–H Functionalization of N-Acyl/Sulfonyl Tetrahydroisoquinolines (THIQs) With Electron-Rich Nucleophiles via 2,3-Dichloro-5,6-Dicyano-1,4-Benzoquinone (DDQ) Oxidation
title_full Direct and Efficient C(sp(3))–H Functionalization of N-Acyl/Sulfonyl Tetrahydroisoquinolines (THIQs) With Electron-Rich Nucleophiles via 2,3-Dichloro-5,6-Dicyano-1,4-Benzoquinone (DDQ) Oxidation
title_fullStr Direct and Efficient C(sp(3))–H Functionalization of N-Acyl/Sulfonyl Tetrahydroisoquinolines (THIQs) With Electron-Rich Nucleophiles via 2,3-Dichloro-5,6-Dicyano-1,4-Benzoquinone (DDQ) Oxidation
title_full_unstemmed Direct and Efficient C(sp(3))–H Functionalization of N-Acyl/Sulfonyl Tetrahydroisoquinolines (THIQs) With Electron-Rich Nucleophiles via 2,3-Dichloro-5,6-Dicyano-1,4-Benzoquinone (DDQ) Oxidation
title_short Direct and Efficient C(sp(3))–H Functionalization of N-Acyl/Sulfonyl Tetrahydroisoquinolines (THIQs) With Electron-Rich Nucleophiles via 2,3-Dichloro-5,6-Dicyano-1,4-Benzoquinone (DDQ) Oxidation
title_sort direct and efficient c(sp(3))–h functionalization of n-acyl/sulfonyl tetrahydroisoquinolines (thiqs) with electron-rich nucleophiles via 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (ddq) oxidation
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7403605/
https://www.ncbi.nlm.nih.gov/pubmed/32850649
http://dx.doi.org/10.3389/fchem.2020.00629
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