Batch and Flow Photochemical Benzannulations Based on the Reaction of Ynamides and Diazo Ketones. Application to the Synthesis of Polycyclic Aromatic and Heteroaromatic Compounds
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Danheiser_Batch and flow.pdf
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Author(s)
Willumstad, Thomas P.
Haze, Olesya
Mak, Xiao Yin
Lam, Tin Yiu
Wang, Yu-Pu
Danheiser, Rick Lane
Date Issued
November 2013
Journal
Journal of Organic Chemistry
Publisher
American Chemical Society (ACS)
Citation
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.
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Author's final manuscript
Abstract
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.
Description
available in PMC 2014 November 1
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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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.
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DOI of Published Version
https://doi.org/10.1021/jo402010b
