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Photoinduced C(sp(3))–H sulfination empowers the direct and chemoselective introduction of the sulfonyl group
Direct installation of the sulfinate group by the functionalization of unreactive aliphatic C–H bonds can provide access to most classes of organosulfur compounds, because of the central position of sulfinates as sulfonyl group linchpins. Despite the importance of the sulfonyl group in synthesis, me...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8549786/ https://www.ncbi.nlm.nih.gov/pubmed/34760178 http://dx.doi.org/10.1039/d1sc04245a |
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author | Jin, Shengfei Haug, Graham C. Trevino, Ramon Nguyen, Viet D. Arman, Hadi D. Larionov, Oleg V. |
author_facet | Jin, Shengfei Haug, Graham C. Trevino, Ramon Nguyen, Viet D. Arman, Hadi D. Larionov, Oleg V. |
author_sort | Jin, Shengfei |
collection | PubMed |
description | Direct installation of the sulfinate group by the functionalization of unreactive aliphatic C–H bonds can provide access to most classes of organosulfur compounds, because of the central position of sulfinates as sulfonyl group linchpins. Despite the importance of the sulfonyl group in synthesis, medicine, and materials science, a direct C(sp(3))–H sulfination reaction that can convert abundant aliphatic C–H bonds to sulfinates has remained elusive, due to the reactivity of sulfinates that are incompatible with typical oxidation-driven C–H functionalization approaches. We report herein a photoinduced C(sp(3))–H sulfination reaction that is mediated by sodium metabisulfite and enables access to a variety of sulfinates. The reaction proceeds with high chemoselectivity and moderate to good regioselectivity, affording only monosulfination products and can be used for a solvent-controlled regiodivergent distal C(sp(3))–H functionalization. |
format | Online Article Text |
id | pubmed-8549786 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-85497862021-11-09 Photoinduced C(sp(3))–H sulfination empowers the direct and chemoselective introduction of the sulfonyl group Jin, Shengfei Haug, Graham C. Trevino, Ramon Nguyen, Viet D. Arman, Hadi D. Larionov, Oleg V. Chem Sci Chemistry Direct installation of the sulfinate group by the functionalization of unreactive aliphatic C–H bonds can provide access to most classes of organosulfur compounds, because of the central position of sulfinates as sulfonyl group linchpins. Despite the importance of the sulfonyl group in synthesis, medicine, and materials science, a direct C(sp(3))–H sulfination reaction that can convert abundant aliphatic C–H bonds to sulfinates has remained elusive, due to the reactivity of sulfinates that are incompatible with typical oxidation-driven C–H functionalization approaches. We report herein a photoinduced C(sp(3))–H sulfination reaction that is mediated by sodium metabisulfite and enables access to a variety of sulfinates. The reaction proceeds with high chemoselectivity and moderate to good regioselectivity, affording only monosulfination products and can be used for a solvent-controlled regiodivergent distal C(sp(3))–H functionalization. The Royal Society of Chemistry 2021-09-28 /pmc/articles/PMC8549786/ /pubmed/34760178 http://dx.doi.org/10.1039/d1sc04245a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/ |
spellingShingle | Chemistry Jin, Shengfei Haug, Graham C. Trevino, Ramon Nguyen, Viet D. Arman, Hadi D. Larionov, Oleg V. Photoinduced C(sp(3))–H sulfination empowers the direct and chemoselective introduction of the sulfonyl group |
title | Photoinduced C(sp(3))–H sulfination empowers the direct and chemoselective introduction of the sulfonyl group |
title_full | Photoinduced C(sp(3))–H sulfination empowers the direct and chemoselective introduction of the sulfonyl group |
title_fullStr | Photoinduced C(sp(3))–H sulfination empowers the direct and chemoselective introduction of the sulfonyl group |
title_full_unstemmed | Photoinduced C(sp(3))–H sulfination empowers the direct and chemoselective introduction of the sulfonyl group |
title_short | Photoinduced C(sp(3))–H sulfination empowers the direct and chemoselective introduction of the sulfonyl group |
title_sort | photoinduced c(sp(3))–h sulfination empowers the direct and chemoselective introduction of the sulfonyl group |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8549786/ https://www.ncbi.nlm.nih.gov/pubmed/34760178 http://dx.doi.org/10.1039/d1sc04245a |
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