Stereospecific Pd-Catalyzed Cross-Coupling Reactions of Secondary Alkylboron Nucleophiles and Aryl Chlorides

[Image: see text] We report the development of a Pd-catalyzed process for the stereospecific cross-coupling of unactivated secondary alkylboron nucleophiles and aryl chlorides. This process tolerates the use of secondary alkylboronic acids and secondary alkyltrifluoroborates and occurs without signi...

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Autores principales: Li, Ling, Zhao, Shibin, Joshi-Pangu, Amruta, Diane, Mohamed, Biscoe, Mark R.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4195375/
https://www.ncbi.nlm.nih.gov/pubmed/25226092
http://dx.doi.org/10.1021/ja508815w
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author Li, Ling
Zhao, Shibin
Joshi-Pangu, Amruta
Diane, Mohamed
Biscoe, Mark R.
author_facet Li, Ling
Zhao, Shibin
Joshi-Pangu, Amruta
Diane, Mohamed
Biscoe, Mark R.
author_sort Li, Ling
collection PubMed
description [Image: see text] We report the development of a Pd-catalyzed process for the stereospecific cross-coupling of unactivated secondary alkylboron nucleophiles and aryl chlorides. This process tolerates the use of secondary alkylboronic acids and secondary alkyltrifluoroborates and occurs without significant isomerization of the alkyl nucelophile. Optically active secondary alkyltrifluoroborate reagents undergo cross-coupling reactions with stereospecific inversion of configuration using this method.
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spelling pubmed-41953752015-09-16 Stereospecific Pd-Catalyzed Cross-Coupling Reactions of Secondary Alkylboron Nucleophiles and Aryl Chlorides Li, Ling Zhao, Shibin Joshi-Pangu, Amruta Diane, Mohamed Biscoe, Mark R. J Am Chem Soc [Image: see text] We report the development of a Pd-catalyzed process for the stereospecific cross-coupling of unactivated secondary alkylboron nucleophiles and aryl chlorides. This process tolerates the use of secondary alkylboronic acids and secondary alkyltrifluoroborates and occurs without significant isomerization of the alkyl nucelophile. Optically active secondary alkyltrifluoroborate reagents undergo cross-coupling reactions with stereospecific inversion of configuration using this method. American Chemical Society 2014-09-16 2014-10-08 /pmc/articles/PMC4195375/ /pubmed/25226092 http://dx.doi.org/10.1021/ja508815w Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html)
spellingShingle Li, Ling
Zhao, Shibin
Joshi-Pangu, Amruta
Diane, Mohamed
Biscoe, Mark R.
Stereospecific Pd-Catalyzed Cross-Coupling Reactions of Secondary Alkylboron Nucleophiles and Aryl Chlorides
title Stereospecific Pd-Catalyzed Cross-Coupling Reactions of Secondary Alkylboron Nucleophiles and Aryl Chlorides
title_full Stereospecific Pd-Catalyzed Cross-Coupling Reactions of Secondary Alkylboron Nucleophiles and Aryl Chlorides
title_fullStr Stereospecific Pd-Catalyzed Cross-Coupling Reactions of Secondary Alkylboron Nucleophiles and Aryl Chlorides
title_full_unstemmed Stereospecific Pd-Catalyzed Cross-Coupling Reactions of Secondary Alkylboron Nucleophiles and Aryl Chlorides
title_short Stereospecific Pd-Catalyzed Cross-Coupling Reactions of Secondary Alkylboron Nucleophiles and Aryl Chlorides
title_sort stereospecific pd-catalyzed cross-coupling reactions of secondary alkylboron nucleophiles and aryl chlorides
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4195375/
https://www.ncbi.nlm.nih.gov/pubmed/25226092
http://dx.doi.org/10.1021/ja508815w
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AT dianemohamed stereospecificpdcatalyzedcrosscouplingreactionsofsecondaryalkylboronnucleophilesandarylchlorides
AT biscoemarkr stereospecificpdcatalyzedcrosscouplingreactionsofsecondaryalkylboronnucleophilesandarylchlorides

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