Cyclic Diaryl λ(3)-Chloranes: Reagents and Their C–C and C–O Couplings with Phenols via Aryne Intermediates

[Image: see text] Hypervalent chloranes are a class of rare and poorly explored reagents. Their unique electronic properties confer reactivity that is complementary to that of the common iodanes and emerging bromanes. Highly chemo- and regioselective, metal-free, and mild C–C and C–O couplings are r...

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Autores principales: Lanzi, Matteo, Rogge, Torben, Truong, Tan Sang, Houk, K. N., Wencel-Delord, Joanna
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9837845/
https://www.ncbi.nlm.nih.gov/pubmed/36535642
http://dx.doi.org/10.1021/jacs.2c10090
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author Lanzi, Matteo
Rogge, Torben
Truong, Tan Sang
Houk, K. N.
Wencel-Delord, Joanna
author_facet Lanzi, Matteo
Rogge, Torben
Truong, Tan Sang
Houk, K. N.
Wencel-Delord, Joanna
author_sort Lanzi, Matteo
collection PubMed
description [Image: see text] Hypervalent chloranes are a class of rare and poorly explored reagents. Their unique electronic properties confer reactivity that is complementary to that of the common iodanes and emerging bromanes. Highly chemo- and regioselective, metal-free, and mild C–C and C–O couplings are reported here. Experimental and computational mechanistic studies elucidate the unprecedented reactivities and selectivities of these systems and the intermediacy of aryne intermediates. The synthetic potential of these transformations is further demonstrated via the post-functionalization of C–C and C–O coupling products obtained from reactions of chloranes with phenols under different conditions.
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spelling pubmed-98378452023-01-14 Cyclic Diaryl λ(3)-Chloranes: Reagents and Their C–C and C–O Couplings with Phenols via Aryne Intermediates Lanzi, Matteo Rogge, Torben Truong, Tan Sang Houk, K. N. Wencel-Delord, Joanna J Am Chem Soc [Image: see text] Hypervalent chloranes are a class of rare and poorly explored reagents. Their unique electronic properties confer reactivity that is complementary to that of the common iodanes and emerging bromanes. Highly chemo- and regioselective, metal-free, and mild C–C and C–O couplings are reported here. Experimental and computational mechanistic studies elucidate the unprecedented reactivities and selectivities of these systems and the intermediacy of aryne intermediates. The synthetic potential of these transformations is further demonstrated via the post-functionalization of C–C and C–O coupling products obtained from reactions of chloranes with phenols under different conditions. American Chemical Society 2022-12-19 /pmc/articles/PMC9837845/ /pubmed/36535642 http://dx.doi.org/10.1021/jacs.2c10090 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Lanzi, Matteo
Rogge, Torben
Truong, Tan Sang
Houk, K. N.
Wencel-Delord, Joanna
Cyclic Diaryl λ(3)-Chloranes: Reagents and Their C–C and C–O Couplings with Phenols via Aryne Intermediates
title Cyclic Diaryl λ(3)-Chloranes: Reagents and Their C–C and C–O Couplings with Phenols via Aryne Intermediates
title_full Cyclic Diaryl λ(3)-Chloranes: Reagents and Their C–C and C–O Couplings with Phenols via Aryne Intermediates
title_fullStr Cyclic Diaryl λ(3)-Chloranes: Reagents and Their C–C and C–O Couplings with Phenols via Aryne Intermediates
title_full_unstemmed Cyclic Diaryl λ(3)-Chloranes: Reagents and Their C–C and C–O Couplings with Phenols via Aryne Intermediates
title_short Cyclic Diaryl λ(3)-Chloranes: Reagents and Their C–C and C–O Couplings with Phenols via Aryne Intermediates
title_sort cyclic diaryl λ(3)-chloranes: reagents and their c–c and c–o couplings with phenols via aryne intermediates
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9837845/
https://www.ncbi.nlm.nih.gov/pubmed/36535642
http://dx.doi.org/10.1021/jacs.2c10090
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