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

Uttam Dutta; Sudip Maiti; Sandeep Pimparkar; Siddhartha Maiti; Lawrence R. Gahan; Elizabeth H. Krenske; David W. Lupton; Debabrata Maiti

doi:10.1039/c9sc01824g

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

Uttam Dutta, Sudip Maiti, Sandeep Pimparkar, Siddhartha Maiti, Lawrence R. Gahan, Elizabeth H. Krenske, David W. Lupton, Debabrata Maiti

School of Chemistry

Research output: Contribution to journal › Article › Research › peer-review

33 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	7426-7432
Number of pages	7
Journal	Chemical Science
Volume	10
Issue number	31
DOIs	https://doi.org/10.1039/c9sc01824g
Publication status	Published - 21 Aug 2019

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Cite this

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title = "Rhodium catalyzed template-assisted distal para-C-H olefination",

abstract = "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.",

author = "Uttam Dutta and Sudip Maiti and Sandeep Pimparkar and Siddhartha Maiti and Gahan, {Lawrence R.} and Krenske, {Elizabeth H.} and Lupton, {David W.} and Debabrata Maiti",

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T1 - Rhodium catalyzed template-assisted distal para-C-H olefination

AU - Dutta, Uttam

AU - Maiti, Sudip

AU - Pimparkar, Sandeep

AU - Maiti, Siddhartha

AU - Gahan, Lawrence R.

AU - Krenske, Elizabeth H.

AU - Lupton, David W.

AU - Maiti, Debabrata

PY - 2019/8/21

Y1 - 2019/8/21

N2 - 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.

AB - 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.

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JO - Chemical Science

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