Rhodium catalyzed template-assisted distal para-C–H olefination

Rhodium catalysis has been extensively used for ortho-C–H functionalization reactions, and successfully extended to meta-C–H functionalization. Its application to para-C–H activation remains an unmet challenge. Herein we disclose the first example of such a reaction, with the Rh-catalyzed para-C–H o...

Descripción completa

Detalles Bibliográficos
Autores principales: Dutta, Uttam, Maiti, Sudip, Pimparkar, Sandeep, Maiti, Siddhartha, Gahan, Lawrence R., Krenske, Elizabeth H., Lupton, David W., Maiti, Debabrata
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2019
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6713868/
https://www.ncbi.nlm.nih.gov/pubmed/31489165
http://dx.doi.org/10.1039/c9sc01824g
_version_ 1783446950536806400
author Dutta, Uttam
Maiti, Sudip
Pimparkar, Sandeep
Maiti, Siddhartha
Gahan, Lawrence R.
Krenske, Elizabeth H.
Lupton, David W.
Maiti, Debabrata
author_facet Dutta, Uttam
Maiti, Sudip
Pimparkar, Sandeep
Maiti, Siddhartha
Gahan, Lawrence R.
Krenske, Elizabeth H.
Lupton, David W.
Maiti, Debabrata
author_sort Dutta, Uttam
collection PubMed
description Rhodium catalysis has been extensively used for ortho-C–H functionalization reactions, and successfully extended to meta-C–H functionalization. Its application to para-C–H activation remains an unmet challenge. Herein we disclose the first example of such a reaction, with the Rh-catalyzed para-C–H olefination of arenes. The use of a Si-linked cyanobiphenyl unit as a traceless directing group leads to highly para-selective arene–olefin couplings.
format Online
Article
Text
id pubmed-6713868
institution National Center for Biotechnology Information
language English
publishDate 2019
publisher Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-67138682019-09-05 Rhodium catalyzed template-assisted distal para-C–H olefination Dutta, Uttam Maiti, Sudip Pimparkar, Sandeep Maiti, Siddhartha Gahan, Lawrence R. Krenske, Elizabeth H. Lupton, David W. Maiti, Debabrata Chem Sci Chemistry Rhodium catalysis has been extensively used for ortho-C–H functionalization reactions, and successfully extended to meta-C–H functionalization. Its application to para-C–H activation remains an unmet challenge. Herein we disclose the first example of such a reaction, with the Rh-catalyzed para-C–H olefination of arenes. The use of a Si-linked cyanobiphenyl unit as a traceless directing group leads to highly para-selective arene–olefin couplings. Royal Society of Chemistry 2019-06-21 /pmc/articles/PMC6713868/ /pubmed/31489165 http://dx.doi.org/10.1039/c9sc01824g Text en This journal is © The Royal Society of Chemistry 2019 http://creativecommons.org/licenses/by-nc/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0)
spellingShingle Chemistry
Dutta, Uttam
Maiti, Sudip
Pimparkar, Sandeep
Maiti, Siddhartha
Gahan, Lawrence R.
Krenske, Elizabeth H.
Lupton, David W.
Maiti, Debabrata
Rhodium catalyzed template-assisted distal para-C–H olefination
title Rhodium catalyzed template-assisted distal para-C–H olefination
title_full Rhodium catalyzed template-assisted distal para-C–H olefination
title_fullStr Rhodium catalyzed template-assisted distal para-C–H olefination
title_full_unstemmed Rhodium catalyzed template-assisted distal para-C–H olefination
title_short Rhodium catalyzed template-assisted distal para-C–H olefination
title_sort rhodium catalyzed template-assisted distal para-c–h olefination
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6713868/
https://www.ncbi.nlm.nih.gov/pubmed/31489165
http://dx.doi.org/10.1039/c9sc01824g
work_keys_str_mv AT duttauttam rhodiumcatalyzedtemplateassisteddistalparacholefination
AT maitisudip rhodiumcatalyzedtemplateassisteddistalparacholefination
AT pimparkarsandeep rhodiumcatalyzedtemplateassisteddistalparacholefination
AT maitisiddhartha rhodiumcatalyzedtemplateassisteddistalparacholefination
AT gahanlawrencer rhodiumcatalyzedtemplateassisteddistalparacholefination
AT krenskeelizabethh rhodiumcatalyzedtemplateassisteddistalparacholefination
AT luptondavidw rhodiumcatalyzedtemplateassisteddistalparacholefination
AT maitidebabrata rhodiumcatalyzedtemplateassisteddistalparacholefination

Ejemplares similares