A simple and practical catalytic electron transfer system composed of TiCl₄ and metallic Yb: application in carbonyl olefination and insight into the mechanism

Abstract

A simple and practical catalytic electron transfer system composed of TiCl4 and Yb, which turned out to be effective for homo- and cross-deoxygenative coupling of aldehydes and ketones was developed. Mechanistic data provide an insight into the rate-determining step and intermediates.

Tetraphenylethylene-Based AIE-Active Probes for Sensing Applications

“…Woollins et al reported the synthesis of 1 in 100% yield by heating 2 equiv of ketone in toluene in the presence of Woollins's reagent. 23 Similarly, the use of ytterbium in combination with TiCl 4 in THF, 24 and a Heck reaction using a phosphapalladacycle catalyst, 25 were also shown to be very effective routes for the production of TPE in ∼99% yield. In another report, Otura et al described the reaction of selenobenzophenone (4) with diphenyldiazomethane (5) in DCM at −78 °C to afford a 76% yield of 1.…”

Fungal Polyketides with Three Distinctive Ring Skeletons from the Fungus Penicillium canescens Uncovered by OSMAC and Molecular Networking Strategies

“…The following tailoring reactions finally assist the formation of structure 1 . Compounds 2 – 4 are supposed polyketide dimers of monomer b , which was constructed by a key cyclization at C-3/C-8 and an aerobic oxidative decarboxylation. , Subsequently, a McMurry-like coupling reaction − in route A or a Claisen reaction in route B happened between two molecules of b to get a dimethyl-substituted double bond or α,β-unsaturated ketone, then selective cyclization and oxidation reactions generate the production of 2 – 4 comprising 6/5/5/6 or 6/6/5/6 heterotetracyclic ring skeletons.…”

Organic Synthesis with Elemental Lanthanides – Going Beyond Samarium and Ytterbium

“…McMurry carbonyl olefination using catalytic TiCl 4 /Yb system. [55] Scheme 28. Initial applications of Cp 2 ZrCl 2 /Ln system.…”