Batch and Flow Photochemical Benzannulations Based on the Reaction of Ynamides and Diazo Ketones. Application to the Synthesis of Polycyclic Aromatic and Heteroaromatic Compounds
available in PMC 2014 November 1
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | en_US |
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American Chemical Society (ACS)
2015
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| Online Access: | http://hdl.handle.net/1721.1/94535 https://orcid.org/0000-0002-9812-206X https://orcid.org/0000-0001-5002-2230 |
| _version_ | 1826214116747902976 |
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| author | Willumstad, Thomas P. Haze, Olesya Mak, Xiao Yin Lam, Tin Yiu Wang, Yu-Pu Danheiser, Rick Lane |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Willumstad, Thomas P. Haze, Olesya Mak, Xiao Yin Lam, Tin Yiu Wang, Yu-Pu Danheiser, Rick Lane |
| author_sort | Willumstad, Thomas P. |
| collection | MIT |
| description | available in PMC 2014 November 1 |
| first_indexed | 2024-09-23T16:00:04Z |
| format | Article |
| id | mit-1721.1/94535 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T16:00:04Z |
| publishDate | 2015 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/945352022-10-02T05:38:35Z Batch and Flow Photochemical Benzannulations Based on the Reaction of Ynamides and Diazo Ketones. Application to the Synthesis of Polycyclic Aromatic and Heteroaromatic Compounds Willumstad, Thomas P. Haze, Olesya Mak, Xiao Yin Lam, Tin Yiu Wang, Yu-Pu Danheiser, Rick Lane Massachusetts Institute of Technology. Department of Chemistry Willumstad, Thomas P. Haze, Olesya Mak, Xiao Yin Lam, Tin Yiu Wang, Yu-Pu Danheiser, Rick Lane available in PMC 2014 November 1 Highly substituted polycyclic aromatic and heteroaromatic compounds are produced via a two-stage tandem benzannulation/cyclization strategy. The initial benzannulation step proceeds via a pericyclic cascade mechanism triggered by thermal or photochemical Wolff rearrangement of a diazo ketone. The photochemical process can be performed using a continuous flow reactor which facilitates carrying out reactions on a large scale and minimizes the time required for photolysis. Carbomethoxy ynamides as well as more ketenophilic bis-silyl ynamines and N-sulfonyl and N-phosphoryl ynamides serve as the reaction partner in the benzannulation step. In the second stage of the strategy, RCM generates benzofused nitrogen heterocycles, and various heterocyclization processes furnish highly substituted and polycyclic indoles of types that were not available by using the previous cyclobutenone-based version of the tandem strategy. National Institutes of Health (U.S.) (GM 28273) National Science Foundation (U.S.) (CHE-1111567) Boehringer Ingelheim Pharmaceuticals AstraZeneca (Firm) (Graduate Fellowship) Massachusetts Institute of Technology (George Buchi Summer Fellowships) Massachusetts Institute of Technology (Merck Fellowship) Massachusetts Institute of Technology (David A. Johnson Fellowship) Massachusetts Institute of Technology (C. P. Chu and Y. Lai Fund) Merck Research Laboratories 2015-02-13T19:48:59Z 2015-02-13T19:48:59Z 2013-11 2013-09 Article http://purl.org/eprint/type/JournalArticle 0022-3263 1520-6904 http://hdl.handle.net/1721.1/94535 Willumstad, Thomas P., Olesya Haze, Xiao Yin Mak, Tin Yiu Lam, Yu-Pu Wang, and Rick L. Danheiser. “Batch and Flow Photochemical Benzannulations Based on the Reaction of Ynamides and Diazo Ketones. Application to the Synthesis of Polycyclic Aromatic and Heteroaromatic Compounds.” The Journal of Organic Chemistry 78, no. 22 (November 15, 2013): 11450–11469. https://orcid.org/0000-0002-9812-206X https://orcid.org/0000-0001-5002-2230 en_US http://dx.doi.org/10.1021/jo402010b Journal of Organic Chemistry 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 | Willumstad, Thomas P. Haze, Olesya Mak, Xiao Yin Lam, Tin Yiu Wang, Yu-Pu Danheiser, Rick Lane Batch and Flow Photochemical Benzannulations Based on the Reaction of Ynamides and Diazo Ketones. Application to the Synthesis of Polycyclic Aromatic and Heteroaromatic Compounds |
| title | Batch and Flow Photochemical Benzannulations Based on the Reaction of Ynamides and Diazo Ketones. Application to the Synthesis of Polycyclic Aromatic and Heteroaromatic Compounds |
| title_full | Batch and Flow Photochemical Benzannulations Based on the Reaction of Ynamides and Diazo Ketones. Application to the Synthesis of Polycyclic Aromatic and Heteroaromatic Compounds |
| title_fullStr | Batch and Flow Photochemical Benzannulations Based on the Reaction of Ynamides and Diazo Ketones. Application to the Synthesis of Polycyclic Aromatic and Heteroaromatic Compounds |
| title_full_unstemmed | Batch and Flow Photochemical Benzannulations Based on the Reaction of Ynamides and Diazo Ketones. Application to the Synthesis of Polycyclic Aromatic and Heteroaromatic Compounds |
| title_short | Batch and Flow Photochemical Benzannulations Based on the Reaction of Ynamides and Diazo Ketones. Application to the Synthesis of Polycyclic Aromatic and Heteroaromatic Compounds |
| title_sort | batch and flow photochemical benzannulations based on the reaction of ynamides and diazo ketones application to the synthesis of polycyclic aromatic and heteroaromatic compounds |
| url | http://hdl.handle.net/1721.1/94535 https://orcid.org/0000-0002-9812-206X https://orcid.org/0000-0001-5002-2230 |
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