Iron-catalyzed directed C2-alkylation and alkenylation of indole with vinylarenes and alkynes
An iron–N-heterocyclic carbene catalyst generated from an iron(III) salt, an imidazolinium salt, and a Grignard reagent promotes alkylation and alkenylation reactions at the indole C2-position with vinylarenes and internal alkynes, respectively, via imine-directed C–H activation. The former reaction...
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sg-ntu-dr.10356-1072152023-02-28T19:38:07Z Iron-catalyzed directed C2-alkylation and alkenylation of indole with vinylarenes and alkynes Yamakawa, Takeshi Yoshikai, Naohiko Wong, Mun Yee School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Organic chemistry::Heterocyclic compounds An iron–N-heterocyclic carbene catalyst generated from an iron(III) salt, an imidazolinium salt, and a Grignard reagent promotes alkylation and alkenylation reactions at the indole C2-position with vinylarenes and internal alkynes, respectively, via imine-directed C–H activation. The former reaction affords 1,1-diarylalkane derivatives with exclusive regioselectivity. Deuterium-labeling experiments suggest that these reactions involve oxidative addition of the C–H bond to the iron center, insertion of the unsaturated bond into the Fe–H bond, and C–C reductive elimination. NRF (Natl Research Foundation, S’pore) Accepted version 2015-04-01T12:53:59Z 2019-12-06T22:26:52Z 2015-04-01T12:53:59Z 2019-12-06T22:26:52Z 2015 2015 Journal Article Wong, M. Y., Yamakawa, T., & Yoshikai, N. (2015). Iron-catalyzed directed C2-alkylation and alkenylation of indole with vinylarenes and alkynes. Organic letters, 17(3), 442-445. https://hdl.handle.net/10356/107215 http://hdl.handle.net/10220/25309 10.1021/ol503395g en Organic letters © 2015 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/ol503395g]. 6 p. application/pdf |
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DRNTU::Science::Chemistry::Organic chemistry::Heterocyclic compounds Yamakawa, Takeshi Yoshikai, Naohiko Wong, Mun Yee Iron-catalyzed directed C2-alkylation and alkenylation of indole with vinylarenes and alkynes |
| description |
An iron–N-heterocyclic carbene catalyst generated from an iron(III) salt, an imidazolinium salt, and a Grignard reagent promotes alkylation and alkenylation reactions at the indole C2-position with vinylarenes and internal alkynes, respectively, via imine-directed C–H activation. The former reaction affords 1,1-diarylalkane derivatives with exclusive regioselectivity. Deuterium-labeling experiments suggest that these reactions involve oxidative addition of the C–H bond to the iron center, insertion of the unsaturated bond into the Fe–H bond, and C–C reductive elimination. |
| author2 |
School of Physical and Mathematical Sciences |
| author_facet |
School of Physical and Mathematical Sciences Yamakawa, Takeshi Yoshikai, Naohiko Wong, Mun Yee |
| format |
Article |
| author |
Yamakawa, Takeshi Yoshikai, Naohiko Wong, Mun Yee |
| author_sort |
Yamakawa, Takeshi |
| title |
Iron-catalyzed directed C2-alkylation and alkenylation of indole with vinylarenes and alkynes |
| title_short |
Iron-catalyzed directed C2-alkylation and alkenylation of indole with vinylarenes and alkynes |
| title_full |
Iron-catalyzed directed C2-alkylation and alkenylation of indole with vinylarenes and alkynes |
| title_fullStr |
Iron-catalyzed directed C2-alkylation and alkenylation of indole with vinylarenes and alkynes |
| title_full_unstemmed |
Iron-catalyzed directed C2-alkylation and alkenylation of indole with vinylarenes and alkynes |
| title_sort |
iron-catalyzed directed c2-alkylation and alkenylation of indole with vinylarenes and alkynes |
| publishDate |
2015 |
| url |
https://hdl.handle.net/10356/107215 http://hdl.handle.net/10220/25309 |
| _version_ |
1759856416931184640 |