Nitrogenation of Alkynes with Nitrones to Prepare Functionalized [1,4]Oxazinones through Csp–Csp<sup>2</sup> Bond Cleavage
Herein, we report a novel strategy of hypervalent iodine(III) compound-mediated selective C<sub>sp</sub>-C<sub>sp</sub><sup>2</sup> bond cleavage of alkynes and C═N/N-O bond cleavage of nitrones and recombination of C-C/C-O/C-N multiple bonds to access various functionalized [1,4]oxazinones bearing a vicinal carbon stereocenter in good yields and high diastereoselectivity. Mechanistic studies revealed that the reaction undergoes a domino [4 + 3] cycloaddition, 1,3-rearrangement of N-O bond, intramolecular cyclization, dearomatization, and rearomatization over four steps in a single flask. The present method features good functional group tolerance, broad substrate scope, and C-C/C═N/N-O multiple bonds cleavage and recombination.
Authors
- L. Yan (ORCID: https://orcid.org/0000-0001-5930-4453)
- Dong‐Liang Mo (ORCID: https://orcid.org/0000-0002-4005-2249)
- Cui Liang (ORCID: https://orcid.org/0000-0001-9356-825X)
- G. Wu
- Xinxian Zhong (ORCID: https://orcid.org/0000-0002-8013-2155)
- Chunhua Chen (ORCID: https://orcid.org/0000-0001-9589-6329)
- Lin-Fen Liao
- Yu Zhao (ORCID: https://orcid.org/0000-0002-7482-3742)
Institutions
- State Ethnic Affairs Commission (CN)
- Guangxi Normal University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-10-25
- DOI
- https://doi.org/10.1021/acs.orglett.4c03553
- Citations
- 5
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 1.25
Funders
- Natural Science Foundation of Guangxi Zhuang Autonomous Region
- National Natural Science Foundation of China
- Scientific Research and Technology Development Program of Guangxi
- Bagui Scholars Program of Guangxi Zhuang Autonomous Region