Visible-Light-Driven Decarboxylative <i>S</i> -Allylation via In Situ Generated Palladium(II) Sulfide Charge-Transfer Complexes: A Sustainable Approach to Allyl Aryl Sulfides
The conventional Pd(0)-catalyzed (2<i>e</i><sup>-</sup> process) has emerged as a powerful approach to catalyze different decarboxylative reactions of γ-methylidene-δ-valerolactones under mild conditions. We found that a combination of triphenylphosphine and palladium(II) sulfides in situ generated from Pd(PPh<sub>3</sub>)<sub>4</sub> and arylthiophenol can catalyze allylation of arylthiophenol by decarboxylative coupling of γ-methylidene-δ-valerolactones through the formation of a charge transfer complex under 427 nm irradiation by blue LEDs, giving a variety of allyl aryl sulfides in good to excellent yields. Mechanistic studies indicate that a radical pathway can account for the decarboxylative C(sp<sup>3</sup>)-S coupling of thiophenols with γ-methylidene-δ-valerolactones, which did not give the corresponding products in the presence of Pd(PPh<sub>3</sub>)<sub>4</sub>.
Authors
- Daoshan Yang (ORCID: https://orcid.org/0000-0002-3047-5416)
- Huiling Mu (ORCID: https://orcid.org/0000-0001-9246-3931)
- Ran Song
- Xin Li (ORCID: https://orcid.org/0000-0001-9050-6504)
- Wen Si (ORCID: https://orcid.org/0000-0002-9850-0702)
- Jiefei Han (ORCID: https://orcid.org/0000-0003-4686-2530)
- Jian Lv (ORCID: https://orcid.org/0000-0001-7641-5411)
Institutions
- Qingdao University of Science and Technology (CN)
- Nanjing Forestry University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-11-16
- DOI
- https://doi.org/10.1021/acs.joc.5c01394
- Primary Topic
- Sulfur-Based Synthesis Techniques
- Type
- article
- Field-Weighted Citation Impact
- 0.00