24188-99-6Relevant articles and documents
Photoredox Reaction of 2-Mercaptothiazolinium Salts with Silyl Enol Ethers
Zemtsov, Artem A.,Ashirbaev, Salavat S.,Levin, Vitalij V.,Kokorekin, Vladimir A.,Korlyukov, Alexander A.,Dilman, Alexander D.
, (2019/11/29)
A method for the generation of free radicals from thiazolinium salts upon photocatalytic reduction is described. The thiazolinium salts are generated by treatment with methyl triflate of 2-mercaptothiazolines, which can be readily obtained from alkyl bromides and tosylates via a nucleophilic substitution reaction or by hydrothiolation of alkenes. Silyl enol ethers were used to trap the radicals, furnishing ketones after successive single-electron oxidation and elimination of the silyl cation.
Tandem intramolecular carbolithiation-transmetallation: From lithium to copper or boron chemistry
Ortiz, Rosa,Yus, Miguel
, p. 1699 - 1707 (2007/10/03)
Lithium/copper transmetallation from the organolithium intermediate 3 (obtained via intramolecular carbolithiation of the acyclic organolithium 2, generated by a chlorine-lithium exchange) gives the corresponding organocopper intermediate 5. This intermediate reacts with eletrophiles, such as allylic or propargylic halides, acyl chlorides or α,β-unsaturated carbonyl compounds giving the expected compounds 6-10, which are not possible to be obtained directly from the organolithium 3. On the other hand, lithium/boron transmetallation affords the corresponding alkylboronic acid 11 which, after palladium-catalysed Suzuki-Miyaura cross-coupling reaction with different aryl bromides gives the expected products 12 with modest yields, the corresponding Ullman biarylic homocoupling products being the major by-products.
