Photocatalytic Strategy for Decyanative Transformations Enabled by Amine-Ligated Boryl Radical
Decyanation after α-functionalization by exploiting the inherent properties of cyano groups enables the strategic assembly of a carbon scaffold. Herein, we demonstrate an amine-ligated boryl radical-mediated cyano group transfer (CGT) strategy of malononitriles under photocatalytic conditions. This strategy allows for the cleavage of C(sp<sup>3</sup>)-CN and the formation of C(sp<sup>3</sup>)-D and C(sp<sup>3</sup>) to realize decyanative deuteration and cyclization via radical-polar crossover. Computational studies successfully demonstrated the reactivity of CGT promoters can be accurately assessed.
Authors
- Kazutake Takada (ORCID: https://orcid.org/0000-0001-9876-2510)
- Shuichi Nakamura (ORCID: https://orcid.org/0000-0001-5633-8367)
- Naoki Yasukawa (ORCID: https://orcid.org/0000-0002-7994-0470)
- Yuto Yoshida (ORCID: https://orcid.org/0009-0005-3576-1859)
- Waka Okada
Institutions
- Nagoya Institute of Technology (JP)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-01-10
- DOI
- https://doi.org/10.1021/acs.orglett.4c04701
- Citations
- 8
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 7.49
Funders
- Takahashi Industrial and Economic Research Foundation
- Japan Society for the Promotion of Science