1067227-27-3Relevant academic research and scientific papers
Development of Palladium-Catalyzed Decarboxylative Allylation of Electron-Deficient Sulfones and Identification of Unusual Side Products
Gill, Monica A.,Manthorpe, Jeffrey M.
, p. 6028 - 6039 (2019/05/24)
The use of sulfones as electron-withdrawing groups in substrates for palladium-catalyzed decarboxylative allylation was explored. A previously published trifluoromethanesulfonyl-based substrate was highly reactive and selective under mild conditions, but the substrate scope was not readily expanded. Instead, 3,5-bis(trifluoromethyl)phenyl sulfones were employed, thereby simultaneously retaining most of the electron deficiency and providing facile synthetic access. Optimization of the catalytic conditions to maximize the product distribution to a synthetically useful level of the allylation product over the protonation side product proved extremely challenging, with inconsistent and irreproducible results afforded with Pd2(dba)3 as the palladium source. A variety of substrates were subjected to the optimized catalytic conditions of PdCp(1-cinnamyl) and Xantphos in tetrahydrofuran at 50 °C for 30 min. These conditions were applicable to all substrates with the exception of the α,α-dimethyl allyl ester, which required more forcing conditions and afforded four products: the allylation and protonation products, as expected, along with a cyclopropylation product and an unprecedented pseudodimeric product. The mechanism for the formation of these unusual side products is considered.
Decarboxylative allylation using sulfones as surrogates of alkanes
Weaver, Jimmie D.,Tunge, Jon A.
supporting information; scheme or table, p. 4657 - 4660 (2009/05/13)
(Chemical Equation Presented) α-Sulfonyl functional groups are traceless activating groups that facilitate catalytic decarboxylative allylations in high yield yet can be cleaved to allow the synthesis of simple allylated alkanes. Substrate studies suggest
