Cyclopropane-Fused N-Heterocycles via Aza-Heck-Triggered C(sp(3))–H Functionalization Cascades

[Image: see text] Unique examples of aza-Heck-based C(sp(3))–H functionalization cascades are described. Under Pd(0)-catalyzed conditions, the aza-Heck-type cyclization of N-(pentafluorobenzoyloxy)carbamates generates alkyl–Pd(II) intermediates that effect C(sp(3))–H palladation en route to cyclopro...

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Autores principales: Jing, Changcheng, Jones, Benjamin T., Adams, Ross J., Bower, John F.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9501755/
https://www.ncbi.nlm.nih.gov/pubmed/36083505
http://dx.doi.org/10.1021/jacs.2c08304
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author Jing, Changcheng
Jones, Benjamin T.
Adams, Ross J.
Bower, John F.
author_facet Jing, Changcheng
Jones, Benjamin T.
Adams, Ross J.
Bower, John F.
author_sort Jing, Changcheng
collection PubMed
description [Image: see text] Unique examples of aza-Heck-based C(sp(3))–H functionalization cascades are described. Under Pd(0)-catalyzed conditions, the aza-Heck-type cyclization of N-(pentafluorobenzoyloxy)carbamates generates alkyl–Pd(II) intermediates that effect C(sp(3))–H palladation en route to cyclopropanes. Key factors that control the site selectivity of the cyclopropanation process have been elucidated such that selective access to a wide range of ring- or spiro-fused systems can be achieved.
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spelling pubmed-95017552022-09-24 Cyclopropane-Fused N-Heterocycles via Aza-Heck-Triggered C(sp(3))–H Functionalization Cascades Jing, Changcheng Jones, Benjamin T. Adams, Ross J. Bower, John F. J Am Chem Soc [Image: see text] Unique examples of aza-Heck-based C(sp(3))–H functionalization cascades are described. Under Pd(0)-catalyzed conditions, the aza-Heck-type cyclization of N-(pentafluorobenzoyloxy)carbamates generates alkyl–Pd(II) intermediates that effect C(sp(3))–H palladation en route to cyclopropanes. Key factors that control the site selectivity of the cyclopropanation process have been elucidated such that selective access to a wide range of ring- or spiro-fused systems can be achieved. American Chemical Society 2022-09-09 2022-09-21 /pmc/articles/PMC9501755/ /pubmed/36083505 http://dx.doi.org/10.1021/jacs.2c08304 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Jing, Changcheng
Jones, Benjamin T.
Adams, Ross J.
Bower, John F.
Cyclopropane-Fused N-Heterocycles via Aza-Heck-Triggered C(sp(3))–H Functionalization Cascades
title Cyclopropane-Fused N-Heterocycles via Aza-Heck-Triggered C(sp(3))–H Functionalization Cascades
title_full Cyclopropane-Fused N-Heterocycles via Aza-Heck-Triggered C(sp(3))–H Functionalization Cascades
title_fullStr Cyclopropane-Fused N-Heterocycles via Aza-Heck-Triggered C(sp(3))–H Functionalization Cascades
title_full_unstemmed Cyclopropane-Fused N-Heterocycles via Aza-Heck-Triggered C(sp(3))–H Functionalization Cascades
title_short Cyclopropane-Fused N-Heterocycles via Aza-Heck-Triggered C(sp(3))–H Functionalization Cascades
title_sort cyclopropane-fused n-heterocycles via aza-heck-triggered c(sp(3))–h functionalization cascades
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9501755/
https://www.ncbi.nlm.nih.gov/pubmed/36083505
http://dx.doi.org/10.1021/jacs.2c08304
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