23586-64-3Relevant articles and documents
Hydrogen-Atom-Transfer-Mediated Acceptorless Dehydrogenative Cross-Coupling Enabled by Multiple Catalytic Functions of Zwitterionic Triazolium Amidate
Minami, Kodai,Ohmatsu, Kohsuke,Ooi, Takashi
, p. 1971 - 1976 (2022/02/07)
An unconventional cooperative catalysis for hydrogen-atom-transfer-mediated acceptorless dehydrogenative cross-coupling is described. The combined use of zwitterionic 1,2,3-triazolium amidate and an Ir-based photosensitizer as catalysts enables C-H/C-H cross-couplings between heteroatom-containing C-H donors and enamides or 1,1-diarylethenes under visible-light irradiation without the need for any oxidants, hydrogen evolution catalysts, or electrodes. A key to establishing this catalysis is the susceptibility of the conjugate acid of the triazolium amidate, amide triazolium, toward single-electron reduction to complete the catalytic cycle.
Alkenylation of unactivated alkyl bromides through visible light photocatalysis
Zhou, Quan-Quan,Düsel, Simon Josef Siegfried,Lu, Liang-Qiu,K?nig, Burkhard,Xiao, Wen-Jing
supporting information, p. 107 - 110 (2019/01/03)
Two visible-light driven alkenylation reactions of unactivated alkyl bromides, which were enabled by the use of Ir(dF(CF3)ppy)2(dtbbpy)PF6 as the photocatalyst and (TMS)3SiH as the atom transfer reagent to activate the alkyl bromides, were described for the first time. These protocols can be used to produce a variety of alkenes from easily available feedstock with good reaction efficiency and high chemoselectivity under mild reaction conditions. To further demonstrate the applicability of the present strategy, the alkenylation of bioactive molecules and glycosyl bromides, as well as the alkynylation of unactivated alkyl bromides, was proven to be feasible.
Photocatalytic decarboxylative alkylations mediated by triphenylphosphine and sodium iodide
Fu, Ming-Chen,Shang, Rui,Zhao, Bin,Wang, Bing,Fu, Yao
, p. 1429 - 1434 (2019/04/30)
Most photoredox catalysts in current use are precious metal complexes or synthetically elaborate organic dyes, the cost of which can impede their application for large-scale industrial processes. We found that a combination of triphenylphosphine and sodium iodide under 456-nanometer irradiation by blue light–emitting diodes can catalyze the alkylation of silyl enol ethers by decarboxylative coupling with redox-active esters in the absence of transition metals. Deaminative alkylation using Katritzky’s N-alkylpyridinium salts and trifluoromethylation using Togni’s reagent are also demonstrated. Moreover, the phosphine/iodide-based photoredox system catalyzes Minisci-type alkylation of N-heterocycles and can operate in tandem with chiral phosphoric acids to achieve high enantioselectivity in this reaction.