Carbon–Carbon Bond Activation with 8-Acylquinolines

Ashley M. Dreis; Christopher J. Douglas

doi:10.1007/128_2013_523

Carbon–Carbon Bond Activation with 8-Acylquinolines

Ashley M. Dreis, Christopher J. Douglas

Chemistry (Twin Cities)

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

15 Scopus citations

Abstract

Synthetically relevant advances in the area of carbon-carbon sigma bond activation have been made possible by 8-acylquinoline directing groups. Stable rhodium metallacycle intermediates have been shown to undergo a variety of transformations, including carboacylation reactions, to produce value-added products containing all-carbon quaternary centers. The kinetic profile of such reactions has been shown to be substrate dependent.

Original language	English (US)
Pages (from-to)	85-110
Number of pages	26
Journal	Topics in Current Chemistry
Volume	346
DOIs	https://doi.org/10.1007/128_2013_523
State	Published - 2014

Bibliographical note

Funding Information:
The authors thank the National Science Foundation (CHE-115157), the donors of the Petroleum Research Fund (47565-G1), and Research Corporation for Science Advancement (Cottrell Scholar Award to CJD, 19985) for support of the work in this chapter carried out at Minnesota.

Publisher Copyright:
© Springer-Verlag Berlin Heidelberg 2014.

Keywords

8-Acylquinoline
8-Quinolinyl ketone
All-carbon quaternary centers
Bond insertion
Carboacylation
Carbon–carbon bond activation
Chelation
Cyclometalation
Directed metalation
Directing group
Metallacycle
Oxidative addition
Rhodium catalyst

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title = "Carbon–Carbon Bond Activation with 8-Acylquinolines",

abstract = "Synthetically relevant advances in the area of carbon-carbon sigma bond activation have been made possible by 8-acylquinoline directing groups. Stable rhodium metallacycle intermediates have been shown to undergo a variety of transformations, including carboacylation reactions, to produce value-added products containing all-carbon quaternary centers. The kinetic profile of such reactions has been shown to be substrate dependent.",

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KW - Chelation

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Carbon–Carbon Bond Activation with 8-Acylquinolines

Abstract

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Keywords

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