Cobalt-catalyzed ortho alkylation of aromatic imines with primary and secondary alkyl halides
We report here cobalt–N-heterocyclic carbene catalytic systems for the ortho alkylation of aromatic imines with alkyl chlorides and bromides, which allows the introduction of a variety of primary and secondary alkyl groups at room temperature. The stereochemical outcomes of the reaction of secondary...
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
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2013
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| Online Access: | https://hdl.handle.net/10356/99605 http://hdl.handle.net/10220/17457 |
| _version_ | 1826127237183700992 |
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| author | Gao, Ke Yoshikai, Naohiko |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Gao, Ke Yoshikai, Naohiko |
| author_sort | Gao, Ke |
| collection | NTU |
| description | We report here cobalt–N-heterocyclic carbene catalytic systems for the ortho alkylation of aromatic imines with alkyl chlorides and bromides, which allows the introduction of a variety of primary and secondary alkyl groups at room temperature. The stereochemical outcomes of the reaction of secondary alkyl halides suggest that the present reaction involves single-electron transfer from a cobalt species to the alkyl halide to generate the corresponding alkyl radical. A cycloalkylated product obtained by this method can be transformed into unique spirocycles through manipulation of the directing and cycloalkyl groups. |
| first_indexed | 2024-10-01T07:05:31Z |
| format | Journal Article |
| id | ntu-10356/99605 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T07:05:31Z |
| publishDate | 2013 |
| record_format | dspace |
| spelling | ntu-10356/996052020-03-07T12:34:48Z Cobalt-catalyzed ortho alkylation of aromatic imines with primary and secondary alkyl halides Gao, Ke Yoshikai, Naohiko School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Organic chemistry We report here cobalt–N-heterocyclic carbene catalytic systems for the ortho alkylation of aromatic imines with alkyl chlorides and bromides, which allows the introduction of a variety of primary and secondary alkyl groups at room temperature. The stereochemical outcomes of the reaction of secondary alkyl halides suggest that the present reaction involves single-electron transfer from a cobalt species to the alkyl halide to generate the corresponding alkyl radical. A cycloalkylated product obtained by this method can be transformed into unique spirocycles through manipulation of the directing and cycloalkyl groups. 2013-11-08T05:39:53Z 2019-12-06T20:09:27Z 2013-11-08T05:39:53Z 2019-12-06T20:09:27Z 2013 2013 Journal Article Gao, K., & Yoshikai, N. (2013). Cobalt-catalyzed ortho alkylation of aromatic imines with primary and secondary alkyl halides. Journal of the American chemical society, 135(25), 9279-9282. https://hdl.handle.net/10356/99605 http://hdl.handle.net/10220/17457 10.1021/ja403759x en Journal of the American chemical society |
| spellingShingle | DRNTU::Science::Chemistry::Organic chemistry Gao, Ke Yoshikai, Naohiko Cobalt-catalyzed ortho alkylation of aromatic imines with primary and secondary alkyl halides |
| title | Cobalt-catalyzed ortho alkylation of aromatic imines with primary and secondary alkyl halides |
| title_full | Cobalt-catalyzed ortho alkylation of aromatic imines with primary and secondary alkyl halides |
| title_fullStr | Cobalt-catalyzed ortho alkylation of aromatic imines with primary and secondary alkyl halides |
| title_full_unstemmed | Cobalt-catalyzed ortho alkylation of aromatic imines with primary and secondary alkyl halides |
| title_short | Cobalt-catalyzed ortho alkylation of aromatic imines with primary and secondary alkyl halides |
| title_sort | cobalt catalyzed ortho alkylation of aromatic imines with primary and secondary alkyl halides |
| topic | DRNTU::Science::Chemistry::Organic chemistry |
| url | https://hdl.handle.net/10356/99605 http://hdl.handle.net/10220/17457 |
| work_keys_str_mv | AT gaoke cobaltcatalyzedorthoalkylationofaromaticimineswithprimaryandsecondaryalkylhalides AT yoshikainaohiko cobaltcatalyzedorthoalkylationofaromaticimineswithprimaryandsecondaryalkylhalides |