Radical 1,2-Boron Shift-Enabled Synthesis of β-Thioalkylboronic Esters from β-Boryl NHPI Esters
A novel protocol for synthesizing β-thioalkylboronic esters via decarboxylative functionalization of β-boronic acid-derived <i>N</i>-hydroxyphthalimide (NHPI) esters is reported. This transformation proceeds under mild conditions with a broad substrate scope and facilitates versatile product derivatization. Mechanistic investigations confirm a radical-mediated 1,2-boron migration pathway. This strategy extends the synthetic utility of radical 1,2-boron migrations from predominant C(sp<sup>3</sup>)-C bond formation to C(sp<sup>3</sup>)-S bond construction, thereby diversifying the reaction landscape of boron migration chemistry.
Authors
- Xinsheng Lei (ORCID: https://orcid.org/0000-0003-1945-4902)
- Guotao Lin
- Qiuling Song (ORCID: https://orcid.org/0000-0002-9836-8860)
- Shiqiang Mu
- Jian Xu (ORCID: https://orcid.org/0000-0002-7881-5416)
- Yu Guo (ORCID: https://orcid.org/0000-0003-4796-8185)
- Y. LIN
- Wenjing Kong
Institutions
- Huaqiao University (CN)
- Chinese Academy of Sciences (CN)
- Shanghai Institute of Organic Chemistry (CN)
- Material Sciences (United States) (US)
- Chemical Synthesis Lab (SG)
- State Key Laboratory of Organometallic Chemistry
- Henan Normal University (CN)
- Fuzhou University (CN)
- Nanjing University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-08-25
- DOI
- https://doi.org/10.1021/acs.orglett.5c03295
- Citations
- 1
- Primary Topic
- Sulfur-Based Synthesis Techniques
- Type
- article
- Field-Weighted Citation Impact
- 0.94
Funders
- National Natural Science Foundation of China