Synthesis of Heterocycles via Pd-Ligand Controlled Cyclization of 2-Chloro-N-(2-vinyl)aniline: Preparation of Carbazoles, Indoles, Dibenzazepines and Acridines
The Pd-catalyzed condensation of 2-bromostyrene and 2-chloroaniline derivatives yields stable diphenylamine intermediates, which are selectively converted to five-, six-, or seven-membered heteroaromatics (indoles, carbazoles, acridines, and dibenzazepines). The selectivity of these intramolecular t...
| Main Authors: | , |
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| Format: | Article |
| Language: | en_US |
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American Chemical Society (ACS)
2012
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| Online Access: | http://hdl.handle.net/1721.1/71969 https://orcid.org/0000-0003-3875-4775 |
| _version_ | 1810981306018824192 |
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| author | Tsvelikhovsky, Dmitry Buchwald, Stephen Leffler |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Tsvelikhovsky, Dmitry Buchwald, Stephen Leffler |
| author_sort | Tsvelikhovsky, Dmitry |
| collection | MIT |
| description | The Pd-catalyzed condensation of 2-bromostyrene and 2-chloroaniline derivatives yields stable diphenylamine intermediates, which are selectively converted to five-, six-, or seven-membered heteroaromatics (indoles, carbazoles, acridines, and dibenzazepines). The selectivity of these intramolecular transformations is uniquely ligand-controlled and offers efficient routes to four important classes of heterocycles from a common precursor. |
| first_indexed | 2024-09-23T10:12:39Z |
| format | Article |
| id | mit-1721.1/71969 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T10:12:39Z |
| publishDate | 2012 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/719692022-09-26T16:26:51Z Synthesis of Heterocycles via Pd-Ligand Controlled Cyclization of 2-Chloro-N-(2-vinyl)aniline: Preparation of Carbazoles, Indoles, Dibenzazepines and Acridines Tsvelikhovsky, Dmitry Buchwald, Stephen Leffler Massachusetts Institute of Technology. Department of Chemistry Buchwald, Stephen L. Tsvelikhovsky, Dmitry Buchwald, Stephen Leffler The Pd-catalyzed condensation of 2-bromostyrene and 2-chloroaniline derivatives yields stable diphenylamine intermediates, which are selectively converted to five-, six-, or seven-membered heteroaromatics (indoles, carbazoles, acridines, and dibenzazepines). The selectivity of these intramolecular transformations is uniquely ligand-controlled and offers efficient routes to four important classes of heterocycles from a common precursor. National Institutes of Health (U.S.) (GM-58160) Novartis AG 2012-08-03T12:49:22Z 2012-08-03T12:49:22Z 2010-09 2010-08 Article http://purl.org/eprint/type/JournalArticle 0002-7863 1520-5126 http://hdl.handle.net/1721.1/71969 Tsvelikhovsky, Dmitry, and Stephen L. Buchwald. “Synthesis of Heterocycles via Pd-Ligand Controlled Cyclization of 2-Chloro-N-(2-vinyl)aniline: Preparation of Carbazoles, Indoles, Dibenzazepines, and Acridines.” Journal of the American Chemical Society 132.40 (2010): 14048–14051. https://orcid.org/0000-0003-3875-4775 en_US http://dx.doi.org/10.1021/ja107511g Journal of the American Chemical Society Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use. application/pdf American Chemical Society (ACS) PMC |
| spellingShingle | Tsvelikhovsky, Dmitry Buchwald, Stephen Leffler Synthesis of Heterocycles via Pd-Ligand Controlled Cyclization of 2-Chloro-N-(2-vinyl)aniline: Preparation of Carbazoles, Indoles, Dibenzazepines and Acridines |
| title | Synthesis of Heterocycles via Pd-Ligand Controlled Cyclization of 2-Chloro-N-(2-vinyl)aniline: Preparation of Carbazoles, Indoles, Dibenzazepines and Acridines |
| title_full | Synthesis of Heterocycles via Pd-Ligand Controlled Cyclization of 2-Chloro-N-(2-vinyl)aniline: Preparation of Carbazoles, Indoles, Dibenzazepines and Acridines |
| title_fullStr | Synthesis of Heterocycles via Pd-Ligand Controlled Cyclization of 2-Chloro-N-(2-vinyl)aniline: Preparation of Carbazoles, Indoles, Dibenzazepines and Acridines |
| title_full_unstemmed | Synthesis of Heterocycles via Pd-Ligand Controlled Cyclization of 2-Chloro-N-(2-vinyl)aniline: Preparation of Carbazoles, Indoles, Dibenzazepines and Acridines |
| title_short | Synthesis of Heterocycles via Pd-Ligand Controlled Cyclization of 2-Chloro-N-(2-vinyl)aniline: Preparation of Carbazoles, Indoles, Dibenzazepines and Acridines |
| title_sort | synthesis of heterocycles via pd ligand controlled cyclization of 2 chloro n 2 vinyl aniline preparation of carbazoles indoles dibenzazepines and acridines |
| url | http://hdl.handle.net/1721.1/71969 https://orcid.org/0000-0003-3875-4775 |
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