A Sterically Tuned Directing Auxiliary Promotes Catalytic 1,2‐Carbofluorination of Alkenyl Carbonyl Compounds

The site‐selective palladium‐catalyzed three‐component coupling of unactivated alkenyl carbonyl compounds, aryl‐ or alkenylboronic acids, and N‐fluorobenzenesulfonimide is described herein. Tuning of the steric environment on the bidentate directing auxiliary enhances regioselectivity and facilitate...

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Autores principales: Liu, Zhonglin, Oxtoby, Lucas J., Sun, Juntao, Li, Zi‐Qi, Kim, Nana, Davies, Geraint H. M., Engle, Keary M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9851970/
https://www.ncbi.nlm.nih.gov/pubmed/36221812
http://dx.doi.org/10.1002/anie.202214153
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author Liu, Zhonglin
Oxtoby, Lucas J.
Sun, Juntao
Li, Zi‐Qi
Kim, Nana
Davies, Geraint H. M.
Engle, Keary M.
author_facet Liu, Zhonglin
Oxtoby, Lucas J.
Sun, Juntao
Li, Zi‐Qi
Kim, Nana
Davies, Geraint H. M.
Engle, Keary M.
author_sort Liu, Zhonglin
collection PubMed
description The site‐selective palladium‐catalyzed three‐component coupling of unactivated alkenyl carbonyl compounds, aryl‐ or alkenylboronic acids, and N‐fluorobenzenesulfonimide is described herein. Tuning of the steric environment on the bidentate directing auxiliary enhances regioselectivity and facilitates challenging C(sp(3))−F reductive elimination from a Pd(IV) intermediate to afford 1,2‐carbofluorination products in moderate to good yields.
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spelling pubmed-98519702023-04-18 A Sterically Tuned Directing Auxiliary Promotes Catalytic 1,2‐Carbofluorination of Alkenyl Carbonyl Compounds Liu, Zhonglin Oxtoby, Lucas J. Sun, Juntao Li, Zi‐Qi Kim, Nana Davies, Geraint H. M. Engle, Keary M. Angew Chem Int Ed Engl Communications The site‐selective palladium‐catalyzed three‐component coupling of unactivated alkenyl carbonyl compounds, aryl‐ or alkenylboronic acids, and N‐fluorobenzenesulfonimide is described herein. Tuning of the steric environment on the bidentate directing auxiliary enhances regioselectivity and facilitates challenging C(sp(3))−F reductive elimination from a Pd(IV) intermediate to afford 1,2‐carbofluorination products in moderate to good yields. John Wiley and Sons Inc. 2022-12-15 2023-01-23 /pmc/articles/PMC9851970/ /pubmed/36221812 http://dx.doi.org/10.1002/anie.202214153 Text en © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ (https://creativecommons.org/licenses/by-nc/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
spellingShingle Communications
Liu, Zhonglin
Oxtoby, Lucas J.
Sun, Juntao
Li, Zi‐Qi
Kim, Nana
Davies, Geraint H. M.
Engle, Keary M.
A Sterically Tuned Directing Auxiliary Promotes Catalytic 1,2‐Carbofluorination of Alkenyl Carbonyl Compounds
title A Sterically Tuned Directing Auxiliary Promotes Catalytic 1,2‐Carbofluorination of Alkenyl Carbonyl Compounds
title_full A Sterically Tuned Directing Auxiliary Promotes Catalytic 1,2‐Carbofluorination of Alkenyl Carbonyl Compounds
title_fullStr A Sterically Tuned Directing Auxiliary Promotes Catalytic 1,2‐Carbofluorination of Alkenyl Carbonyl Compounds
title_full_unstemmed A Sterically Tuned Directing Auxiliary Promotes Catalytic 1,2‐Carbofluorination of Alkenyl Carbonyl Compounds
title_short A Sterically Tuned Directing Auxiliary Promotes Catalytic 1,2‐Carbofluorination of Alkenyl Carbonyl Compounds
title_sort sterically tuned directing auxiliary promotes catalytic 1,2‐carbofluorination of alkenyl carbonyl compounds
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9851970/
https://www.ncbi.nlm.nih.gov/pubmed/36221812
http://dx.doi.org/10.1002/anie.202214153
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