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Selective sulfonylation and isonitrilation of para-quinone methides employing TosMIC as a source of sulfonyl group or isonitrile group

Chemoselective sulfonylation and isonitrilation reactions for the divergent synthesis of valuable diarylmethyl sulfones and isonitrile diarylmethanes starting from easy-to-synthesize para-quinone methides (p-QMs) and commercially abundant p-toluenesulfonylmethyl isocyanide (TosMIC) by using respecti...

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Autores principales: Qu, Chuanhua, Huang, Run, Li, Yong, Liu, Tong, Chen, Yuan, Song, Guiting
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8649203/
https://www.ncbi.nlm.nih.gov/pubmed/34925621
http://dx.doi.org/10.3762/bjoc.17.193
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author Qu, Chuanhua
Huang, Run
Li, Yong
Liu, Tong
Chen, Yuan
Song, Guiting
author_facet Qu, Chuanhua
Huang, Run
Li, Yong
Liu, Tong
Chen, Yuan
Song, Guiting
author_sort Qu, Chuanhua
collection PubMed
description Chemoselective sulfonylation and isonitrilation reactions for the divergent synthesis of valuable diarylmethyl sulfones and isonitrile diarylmethanes starting from easy-to-synthesize para-quinone methides (p-QMs) and commercially abundant p-toluenesulfonylmethyl isocyanide (TosMIC) by using respectively zinc iodide and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as catalysts were developed. The distinguishing feature of this method is that TosMIC plays a dual role from the same substrates in the reaction: as a sulfonyl source or as an isonitrile source. The synthetic utility of this protocol was also demonstrated in the synthesis of difluoroalkylated diarylmethane 5 and diarylmethane ketone derivatives 6 and 7, which are important core structures in natural products and medicines.
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spelling pubmed-86492032021-12-16 Selective sulfonylation and isonitrilation of para-quinone methides employing TosMIC as a source of sulfonyl group or isonitrile group Qu, Chuanhua Huang, Run Li, Yong Liu, Tong Chen, Yuan Song, Guiting Beilstein J Org Chem Full Research Paper Chemoselective sulfonylation and isonitrilation reactions for the divergent synthesis of valuable diarylmethyl sulfones and isonitrile diarylmethanes starting from easy-to-synthesize para-quinone methides (p-QMs) and commercially abundant p-toluenesulfonylmethyl isocyanide (TosMIC) by using respectively zinc iodide and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as catalysts were developed. The distinguishing feature of this method is that TosMIC plays a dual role from the same substrates in the reaction: as a sulfonyl source or as an isonitrile source. The synthetic utility of this protocol was also demonstrated in the synthesis of difluoroalkylated diarylmethane 5 and diarylmethane ketone derivatives 6 and 7, which are important core structures in natural products and medicines. Beilstein-Institut 2021-12-02 /pmc/articles/PMC8649203/ /pubmed/34925621 http://dx.doi.org/10.3762/bjoc.17.193 Text en Copyright © 2021, Qu et al. https://creativecommons.org/licenses/by/4.0/This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.
spellingShingle Full Research Paper
Qu, Chuanhua
Huang, Run
Li, Yong
Liu, Tong
Chen, Yuan
Song, Guiting
Selective sulfonylation and isonitrilation of para-quinone methides employing TosMIC as a source of sulfonyl group or isonitrile group
title Selective sulfonylation and isonitrilation of para-quinone methides employing TosMIC as a source of sulfonyl group or isonitrile group
title_full Selective sulfonylation and isonitrilation of para-quinone methides employing TosMIC as a source of sulfonyl group or isonitrile group
title_fullStr Selective sulfonylation and isonitrilation of para-quinone methides employing TosMIC as a source of sulfonyl group or isonitrile group
title_full_unstemmed Selective sulfonylation and isonitrilation of para-quinone methides employing TosMIC as a source of sulfonyl group or isonitrile group
title_short Selective sulfonylation and isonitrilation of para-quinone methides employing TosMIC as a source of sulfonyl group or isonitrile group
title_sort selective sulfonylation and isonitrilation of para-quinone methides employing tosmic as a source of sulfonyl group or isonitrile group
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8649203/
https://www.ncbi.nlm.nih.gov/pubmed/34925621
http://dx.doi.org/10.3762/bjoc.17.193
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