Rhodium(III)-catalyzed directed peri-C-H alkenylation of anthracene derivatives

Rhodium(III)-catalyzed directed peri-C-H alkenylation of anthracene derivatives

Rhodium(III)-catalyzed oxidative coupling reactions of anthracene-9-carboxylic acid derivatives with electron-deficient olefins are reported. A cationic rhodium(III) catalyst, in combination with a copper(II) oxidant, promotes selective monoalkenylation of anthracene-9-carboxamide, affording 1-alken...

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Main Authors: Karthikeyan, Jaganathan, Yoshikai, Naohiko
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2014
Subjects:
DRNTU::Science::Chemistry::Organic chemistry
Online Access:https://hdl.handle.net/10356/103704
http://hdl.handle.net/10220/24543
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-1037042023-02-28T19:29:16Z Rhodium(III)-catalyzed directed peri-C-H alkenylation of anthracene derivatives Karthikeyan, Jaganathan Yoshikai, Naohiko School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Organic chemistry Rhodium(III)-catalyzed oxidative coupling reactions of anthracene-9-carboxylic acid derivatives with electron-deficient olefins are reported. A cationic rhodium(III) catalyst, in combination with a copper(II) oxidant, promotes selective monoalkenylation of anthracene-9-carboxamide, affording 1-alkenylanthracene-9-carboxamide in moderate to good yields. A similar catalytic system also promotes the reaction of anthracene-9-carboxylic acid and an electron-deficient olefin, which affords a lactone derivative through C–H alkenylation followed by intramolecular conjugate addition. NRF (Natl Research Foundation, S’pore) Accepted version 2014-12-26T06:09:52Z 2019-12-06T21:18:24Z 2014-12-26T06:09:52Z 2019-12-06T21:18:24Z 2014 2014 Journal Article Karthikeyan, J., & Yoshikai, N. (2014). Rhodium(III)-catalyzed directed peri-C-H alkenylation of anthracene derivatives. Organic letters, 16(16), 4224-4227. https://hdl.handle.net/10356/103704 http://hdl.handle.net/10220/24543 10.1021/ol501926b en Organic letters © 2014 American Chemical Society. This is the author created version of a work that has been peer reviewed and accepted for publication by Organic Letters, American Chemical Society. It incorporates referee’s comments but changes resulting from the publishing process, such as copyediting, structural formatting, may not be reflected in this document. The published version is available at: [http://dx.doi.org/10.1021/ol501926b]. 5 p. application/pdf
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic DRNTU::Science::Chemistry::Organic chemistry
spellingShingle DRNTU::Science::Chemistry::Organic chemistry
Karthikeyan, Jaganathan
Yoshikai, Naohiko
Rhodium(III)-catalyzed directed peri-C-H alkenylation of anthracene derivatives
description Rhodium(III)-catalyzed oxidative coupling reactions of anthracene-9-carboxylic acid derivatives with electron-deficient olefins are reported. A cationic rhodium(III) catalyst, in combination with a copper(II) oxidant, promotes selective monoalkenylation of anthracene-9-carboxamide, affording 1-alkenylanthracene-9-carboxamide in moderate to good yields. A similar catalytic system also promotes the reaction of anthracene-9-carboxylic acid and an electron-deficient olefin, which affords a lactone derivative through C–H alkenylation followed by intramolecular conjugate addition.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Karthikeyan, Jaganathan
Yoshikai, Naohiko
format Article
author Karthikeyan, Jaganathan
Yoshikai, Naohiko
author_sort Karthikeyan, Jaganathan
title Rhodium(III)-catalyzed directed peri-C-H alkenylation of anthracene derivatives
title_short Rhodium(III)-catalyzed directed peri-C-H alkenylation of anthracene derivatives
title_full Rhodium(III)-catalyzed directed peri-C-H alkenylation of anthracene derivatives
title_fullStr Rhodium(III)-catalyzed directed peri-C-H alkenylation of anthracene derivatives
title_full_unstemmed Rhodium(III)-catalyzed directed peri-C-H alkenylation of anthracene derivatives
title_sort rhodium(iii)-catalyzed directed peri-c-h alkenylation of anthracene derivatives
publishDate 2014
url https://hdl.handle.net/10356/103704
http://hdl.handle.net/10220/24543
_version_ 1759857817739591680

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