21985-98-8

Upstream product

• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 431-03-8 dimethylglyoxal 
• 99-91-2 para-chloroacetophenone 
• 98-86-2 acetophenone 
• 917-54-4 methyllithium 
• 122-01-0 4-chloro-benzoyl chloride 
• 119-61-9 benzophenone 
• 134-85-0 4-chlorobenzophenone 

Downstream Products

• 6325-06-0 3,3-Bis(4-chlorphenyl)-2-butanon 
• 74-11-3 para-chlorobenzoic acid 
• 99-91-2 para-chloroacetophenone 
• 75416-78-3 4,4'-(buta-1,3-diene-2,3-diyl)bis(chlorobenzene) 
• 100865-80-3 2,2-bis(4-chlorophenyl)propanoic acid 
• 62544-01-8 3,4-Bis-(4-chloro-phenyl)-cyclohex-3-enecarboxylic acid 

Relevant academic research and scientific papers

Zn-AlCl3 · 6H2O-mediated reaction in aqueous media: Pinacol coupling reaction

(Chemical Equation Presented) Vicinal diols have been prepared in good yield by pinacol coupling reaction of aromatic aldehydes and ketones with commercially available zinc and AlCl3 · 6H2O in water. Copyright Taylor & Francis Group, LLC.

Light-enabled metal-free pinacol coupling by hydrazine

Efficient carbon-carbon bond formation is of great importance in modern organic synthetic chemistry. The pinacol coupling discovered over a century ago is still one of the most efficient coupling reactions to build the C-C bond in one step. However, traditional pinacol coupling often requires over-stoichiometric amounts of active metals as reductants, causing long-lasting metal waste issues and sustainability concerns. A great scientific challenge is to design a metal-free approach to the pinacol coupling reaction. Herein, we describe a light-driven pinacol coupling protocol without use of any metals, but with N2H4, used as a clean non-metallic hydrogen-atom-transfer (HAT) reductant. In this transformation, only traceless non-toxic N2 and H2 gases were produced as by-products with a relatively broad aromatic ketone scope and good functional group tolerance. A combined experimental and computational investigation of the mechanism suggests that this novel pinacol coupling reaction proceeds via a HAT process between photo-excited ketone and N2H4, instead of the common single-electron-transfer (SET) process for metal reductants.

Simple and expeditious pinacol coupling of non usual α,β-unsaturated carbonyl compounds in water

Using zinc (0) in a 5% v AcOH aqueous solution allowed the efficient pinacol coupling of aliphatic or aromatic unusual, α,β-unsaturated carbonyl compounds such as citral A in good to excellent yields (56-99%). It can also be successfully applied to acetophenone.

Mg/Triethylammonium formate: A useful system for reductive dimerization of araldehydes into pinacols; Nitroarenes into azoarenes and azoarenes into hydrazoarenes

Studies are reported which describes the effectiveness of triethylammonium formate in the presence of magnesium for the efficient intermolecular pinacol coupling using MeOH as solvent, Various aromatic carbonyls underwent smooth reductive coupling to give the corresponding I ,2-diols. A series of azo compounds were obtained by the reductive coupling of nitroaromatics while azo compounds were reduced to the corresponding hydrazoarenes by this system. There was no adverse effect on the other reducible and hydrogenolysable groups such as ether linkage, hydroxy and halogens. The reactions are clean, high yielding and inexpensive. All the reactions proceeded smoothly at ambient temperature.

Unusual structure and reactivity of a homoleptic "super-ate" complex of iron: Implications for Grignard additions, cross-coupling reactions, and the Kharasch deconjugation

The additional molecule of methyllithium present in [(Me 4Fe)(MeLi)][Li(OEt2)]2 (1), the first structurally characterized ate complex of FeII bearing only alkyl substituents without any further stabilizing ligands (see picture: Fe: magenta; Li: cyan; O: red; C and H: gray), is a particularly remarkable structural feature and contributes to the fascinating reactivity profile of 1 in the title reactions. (Chemical Equation Presented).

Pinacol coupling of carbonyl compounds by using Al-NaOH/MeOH under microwave irradiation

Reductive coupling of aromatic aldehydes and ketones to the corresponding 1,2-diols has been achieved in 59-98% yields using aluminium powder in aqueous sodium hydroxide and methanol medium under microwave irradiation for 5-12 min. The notable advantage of this method seems to be negligible formation of simple amounts of reduced product of the carbonyls i.e. alcohols and the formation of side product olefins via McMurry coupling. The reaction rate is fast and the purity of products is compared to the existing methods. The potential Pinacol rearrangement of the reductive coupling products greatly extends their synthetic utility.

Zirconocene dichloride-catalyzed pinacol coupling of aromatic aldehydes and ketones

The reductive coupling of aromatic aldehydes and ketones has been achieved using a catalytic amount of zirconocene dichloride in the presence of magnesium metal and chlorotrimethylsilane in THF at room temperature to afford the corresponding 1,2-diols in good yields and diastereoselectivity. Copyright Taylor & Francis Group, LLC.

Samarium-induced convenient reductive dimerization of aromatic ketones in aqueous methanol: A mechanistic approach

Samarium metal has been used for the reductive dimerization of aromatic ketones in the presence of additives; the most probable mechanism has been advanced to explain the diastereoselectivity of this dimerization reaction.

Reductive coupling of aromatic aldehydes to pinacols using active manganese under ultrasound irradiation

The pinacol coupling of aromatic aldehydes has been carried out in 30-98% yield with active manganese at r.t. for 2 hr under ultrasound irradiation. The main advantages of the present procedure are shorter reaction time, less reagent (manganese) and higher yield of pinacols.

Magnesium-induced pinacol coupling of aromatic aldehydes and ketones in water under ultrasound

The pinacol coupling of aromatic aldehydes and ketones has been carried out in 20-62% and 10-91% yields, respectively with Mg and Mg-MgCl2 in water under ultrasound irradiation at room temperature for 3-4hr.