40730-41-4Relevant articles and documents
The palladium-catalyzed cross-coupling reaction of 9-organothio-9-borabicyclo[3.3.1]nonanes with organic electrophiles: Synthesis of unsymmetrical sulfides
Ishiyama, Tatsuo,Mori, Masashi,Suzuki, Akira,Miyaura, Norio
, p. 225 - 231 (1996)
The synthesis of unsymmetrical sulfides was carried out in high yields by the palladium-catalyzed cross-coupling reaction of 9-organothio-9-borabicyclo[3.3.1]nonane (9-RS-9-BBN) with organic electrophiles, such as iodoarenes, 1-iodo-1-alkenes, allyl carbonate and propargyl carbonate. Iodoarenes and 1-iodo-1-atkenes were smoothly converted into the corresponding sulfides at 50 °C in the presence of PdC12(dppf) (3 mol%) and K3PO4 (3 equiv.) in DMF. In contrast, the cross-coupling reaction of 9-RS-9-BBN with allyl or propargyl carbonates occurred in DMF without the assistance of a base. Both reactions catalyzed by Pd(dba)2-dppf regioselectively produced allyl and allenyl sulfides in excellent yields. The scope and limitations of the reactions, as well as the effects of varying the reaction conditions, are discussed.
Pd-Catalyzed Double-Decarbonylative Aryl Sulfide Synthesis through Aryl Exchange between Amides and Thioesters
Bie, Fusheng,Cao, Han,Liu, Chengwei,Liu, Xuejing,Shi, Yijun,Szostak, Michal,Zhou, Tongliang
, p. 8098 - 8103 (2021/10/25)
We report the palladium-catalyzed double-decarbonylative synthesis of aryl thioethers by an aryl exchange reaction between amides and thioesters. In this method, amides serve as aryl donors and thioesters are sulfide donors, enabling the synthesis of valuable aryl sulfides. The use of Pd/Xantphos without any additives has been identified as the catalytic system promoting the aryl exchange by C(O)-N/C(O)-S cleavages. The method is amenable to a wide variety of amides and sulfides.
Engaging Ag(0) single atoms in silver(I) salts-mediated C-B and C-S coupling under visible light irradiation
Cui, Enxin,Guo, Lirong,Li, Haibin,Qiao, Dan,Tung, Chen-Ho,Wang, Yifeng
, p. 255 - 263 (2021/09/06)
Silver(I) salts were found active in the borylation and sulfenylation of aryl iodides under visible light irradiation. The optimized borylation protocol using AgF did not need any additive, operated under very mild conditions, and well tolerated a broad scope of substrates and boron sources. Formation of Ag(0) single atoms (AgSAs) during the borylation reactions was examined using high-angle annular dark field aberration-corrected scanning transmission electron microscope (HAADF AC-STEM) and electron paramagnetic resonance (EPR). The activities of the silver(I) salts were affected by the anions and could be associated with their abilities in formation of AgSAs during the reactions. Kinetic studies showed that the deiodination rate was linearly correlated with the loading of AgSAs, and hence AgSAs were the true catalytic centers for the 1e?-reduction of the C-I moieties. The oxidation state of AgSAs kept 0 in both the resting and the working states. A “work-in-tandem” mechanism involving AgSAs as the catalytic centers and AgNPs as the light absorber to achieve the borylation of aryl iodides under visible light irradiation is proposed. The current approach not only provides an alternative system for borylation and sulfenylation of aryl iodides, but also reveals a new activity of silver(I) salts involving AgSAs under visible light irradiation.
