23586-64-3

Upstream product

• 4250-82-2 (3,3-dimethyl-but-1-ynyl)benzene 
• 841-76-9 triphenylaluminium 
• 530-48-3 1,1-Diphenylethylene 
• 38442-51-2 tert-butylmercury chloride 
• 19997-66-1 1-iodo-2,2-diphenylethylene 
• 26189-62-8 phenyl 2,2-diphenylethenyl sulfone 
• 91083-76-0 Ph₂CCHSnBu₃ 
• 67341-86-0 Ph₂CCHHgBr 
• 98-83-9 isopropenylbenzene 
• 32636-65-0 diphenylmethyl diethyl phosphate 
• 630-19-3 pivalaldehyde 
• 98-80-6 phenylboronic acid 
• 22072-53-3 Ph₂CCHMgBr 
• 24522-19-8 Ph₂CCHHgCl 

Downstream Products

• 104142-12-3 3,3-Dimethyl-1,1-di(4-nitrophenyl)butan 
• 55190-54-0 Benzhydryldimethylcyclopropan 

Relevant academic research and scientific papers

Hydrogen-Atom-Transfer-Mediated Acceptorless Dehydrogenative Cross-Coupling Enabled by Multiple Catalytic Functions of Zwitterionic Triazolium Amidate

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.

Decarbonylative cascade cyclization of ortho-cyanoarylacrylamides with pivaldehyde: Access to tert-butyl containing quinolone-2,4(1H,3H)-diones

A TBPB initiated decarbonylative cascade cyclization of ortho-cyanoarylacrylamides with pivaldehyde leads to tert-butyl containing quinolone-2,4(1H,3H)-diones by formation of both C(sp3)–C(sp3) and C(sp3)–C(sp2) bonds. The reaction features simple reaction conditions and convenient reagents. Two radical additions are involved in the transformation.

Alkenylation of unactivated alkyl bromides through visible light photocatalysis

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.

Dual nickel- and photoredox-catalyzed reductive cross-coupling of aryl vinyl halides and unactivated tertiary alkyl bromides

A novel reductive cross-coupling of aryl vinyl halides and unactivated tertiary alkyl bromides has been realized via photoredox/nickel dual catalysis to produce vinyl arene derivatives bearing all-carbon quaternary centers with excellent E-selectivity. A stoichiometric metal reductant could be avoided by employing commercially available N,N,N′,N′-tetramethylethylenediamine (TMEDA) as the terminal reductant.

Photocatalytic decarboxylative alkylations mediated by triphenylphosphine and sodium iodide

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.

3-tert-Butyl-Substituted Cyclohexa-1,4-dienes as Isobutane Equivalents in the B(C6F5)3-Catalyzed Transfer Hydro-tert-Butylation of Alkenes

Cyclohexa-1,4-dienes with a tert-butyl group at C3 are shown to function as isobutane equivalents when activated by the strong boron Lewis acid tris(pentafluorophenyl)borane. The hitherto unprecedented transfer hydro-tert-butylation from one unsaturated hydrocarbon to another is achieved with 1,1-diarylalkenes as substrates, thereby presenting itself as a new way of incorporating tertiary alkyl groups into carbon frameworks. Transient carbocation intermediates give rise to competing reaction pathways that could not be fully suppressed.

Metal-Free Cascade Oxidative Decarbonylative Alkylation/Arylation of Alkynoates with Alphatic Aldehydes

The oxidative difunctionalization of aryl alkynoates with alphatic aldehydes as a cheap and abundant alkyl radical source was developed, providing a variety of trisubstituted alkenes in moderate to good yields. In this reaction, radical decarbonylative alkylation of C-C triple bond, 1,4-aryl migration, and decarboxylation were involved under metal-free conditions.

Intermolecular Photocatalyzed Heck-like Coupling of Unactivated Alkyl Bromides by a Dinuclear Gold Complex

A practical protocol for a photocatalyzed alkyl-Heck-like reaction of unactivated alkyl bromides and different alkenes promoted by dinuclear gold photoredox catalysis in the presence of an inorganic base is reported. Primary, secondary, and tertiary unactivated alkyl bromides with β-hydrogen can be applied. Esters, aldehydes, ketones, nitriles, alcohols, heterocycles, alkynes, alkenes, ethers, and halogen moieties are all well tolerated. In addition to 1,1-diarylalkenes, silylenolethers and enamides can also be applied, which further increases the synthetic potential of the reaction. The mild reaction conditions, broad substrate scope, and an excellent functional-group tolerance deliver an ideal tool for synthetic chemists that can even be used for challenging late-stage modifications of complex natural products.

Silver-catalyzed regioselective carbomagnesiation of alkynes with alkyl halides and Grignard reagents

A silver-catalyzed carbomagnesiation of alkynes with alkyl halides and Grignard reagents afforded alkenyl Grignard reagents regioselectively, where the alkyl group of the alkyl halide, but not that of the Grignard reagent, was introduced into the alkyne.

Ni-catalyzed regioselective three-component coupling of alkyl halides, arylalkynes, or enynes with R-M (M = MgX′, ZnX′)

A new method for the regioselective three-component cross-coupling of alkyl halides, alkynes, or enynes with organomagnesium or organozinc reagents in the presence of a nickel catalyst and a dppb ligand has been developed.