Photocatalyzed Direct C(sp<sup>3</sup>)–H Alkenylation of Unactivated Alkanes via Tandem C–C Activation of Cyclopropenes
A highly adaptable method has been developed for the alkenylation of a broad spectrum of inert alkanes, employing milder reaction conditions. Tetrabutylammonium decatungstate (TBADT) serves as a photocatalyst for hydrogen atom transfer (HAT), instigating the formation of transient alkyl radicals through C(sp<sup>3</sup>)-H functionalization. These radicals exhibit regioselective addition to cyclopropenes, followed by the subsequent activation of C-C bonds, forming the corresponding vinylated derivatives. This methodology accommodates diverse unreactive C(sp<sup>3</sup>)-H bond motifs and multisubstituted cyclopropenes, enabling the efficient synthesis of highly functionalized olefins with high diastereoselectivity.
Authors
- Palasetty Chandu (ORCID: https://orcid.org/0000-0001-5776-5651)
- Sourabh Biswas (ORCID: https://orcid.org/0000-0001-6187-8106)
- Debabrata Das (ORCID: https://orcid.org/0000-0003-4326-6805)
- Devarajulu Sureshkumar (ORCID: https://orcid.org/0000-0002-6985-3496)
- Koustav Pal
Institutions
- Indian Institute of Science Education and Research Kolkata (IN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-08-16
- DOI
- https://doi.org/10.1021/acs.joc.4c01378
- Citations
- 7
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 1.75
Funders
- Council of Scientific and Industrial Research, India
- University Grants Committee
- Indian Institute of Science Education and Research Kolkata
- Science and Engineering Research Board