86130-04-3

Upstream product

• 3597-91-9 biphenyl-4-yl methanol 
• 3218-36-8 4-Phenylbenzaldehyde 
• 107-05-1 3-chloroprop-1-ene 
• 106-95-6 allyl bromide 
• 104-88-1 4-chlorobenzaldehyde 

Downstream Products

• 4746-80-9 4,4'-diphenylbenzil 

Relevant academic research and scientific papers

CBZ6 as a Recyclable Organic Photoreductant for Pinacol Coupling

A recyclable organic photoreductant (1 mol % CBZ6)-catalyzed reductive (pinacol) coupling of aldehydes, ketones, and imines has been developed. Irradiated by purple light (407 nm) using triethylamine as an electron donor, a variety of 1,2-diols and 1,2-diamines could be prepared. The oxidation potential of the excited state of CBZ6 is established as -1.92 V (vs saturated calomel electrode (SCE)). The relative high reductive potential enables the reductive coupling of carbonyl compounds and their derivatives. CBZ6 can be prepared in gram scale and is acid/base- or air-stable. It could be applied in large-scale photoreductive synthesis and recovered in high yield after the reaction.

Photoredox Allylation Reactions Mediated by Bismuth in Aqueous Conditions

Organometallic allylic reagents are widely used in the construction of C?C bonds by Barbier-type reactions. In this communication, we have described a photoredox Barbier allylation of aldehydes mediated by bismuth, in absence of other metals as co-reductants. Mild reaction conditions, tolerance of oxygen, and use of aqueous solvent make this photoredox methodology attractive for green and sustainable synthesis of homoallylic alcohols.

Application of coumarin dyes for organic photoredox catalysis

Here we report the application of readily prepared and available coumarin dyes for photoredox catalysis, which are able to mimic powerful reductant [Ir(iii)] complexes. Coumarin derivatives 9 and 10 were employed as photoreductants in pinacol coupling and in other reactions, in the presence of Et3N as a sacrificial reducing agent. As the electronic, photophysical, and steric properties of coumarins could be varied, a wide applicability to several classes of photoredox reactions is predicted.

Photoredox-Catalyzed Reductive Coupling of Aldehydes, Ketones, and Imines with Visible Light

Ketyl radical and amino radical anions, valuable reactive intermediates for C-C bond-forming reactions, are accessible through a C=O/C=NR umpolung. However, their utilization in catalysis remains largely underdeveloped owing to the high reduction potential of carbonyl compounds and imines. In the context of photoredox catalysis, tertiary amines are commonly employed as sacrificial co-reducing agents. Herein, an additional role of the amine is proposed, in which it is essential for the organocatalytic substrate activation. The combination of photoredox catalysis and carbonyl/imine activation enables the reductive coupling of aldehydes, ketones, and imines under mild reaction conditions.

Synthesis of ferrocene derivatives with planar chirality via palladium-catalyzed enantioselective C-H bond activation

The first catalytic and enantioselective C-H direct acylation of ferrocene derivatives has been developed. A series of 2-acyl-1-dimethylaminomethylferrocenes with planar chirality were provided under highly efficient and concise one-pot conditions with up to 85% yield and 98% ee. The products obtained could be easily converted to various chiral ligands via diverse transformations.

Highly diastereoselective pinacol coupling of aldehydes catalyzed by titanium-schiff base complexes

A new effective methodology for a highly diastereoselective pinacol coupling of aldehydes is described. The method employes 3 mol % of a complex prepared in situ from TiCl4(THF)2 and a Schiff base in acetonitrile. The catalytic cycle is realized with Me3SiCl and Mn as reducing agent. The dependence of the diastereoselectivity on the Schiff base used is reported.

The first catalytic enantioselective Nozaki-Hiyama reaction

The Nozaki-Hiyama reaction can be performed in an enantioselective catalytic way! The catalytic system utilizes 10 mol % of an inexpensive chiral [Cr(salen)] complex. The [Cr(salen)]/Mn/Me3SiCl system effectively promotes the enantioselective addition of allyl chloride to aliphatic and aromatic aldehydes at room temperature (65-89% ee, 40-60% yield).

Titanocene-catalyzed pinacol couplings: Reagent-controlled transition-metal-catalyzed radical reactions

The titanocene-catalyzed pinacol coupling of aromatic aldehydes proceeding in good yields and with high diastereoselectivity under reagent control is described.

Manganese-mediated carbon-carbon bond formation in aqueous media: Chemoselective allylation and pinacol coupling of aryl aldehydes

The use of manganese as a mediator for allylations and pinacol couplings in aqueous media was investigated. The combination of manganese and copper is found to be a highly effective mediator for the allylation of aryl aldehydes in water. Such a combination is found to be more reactive than other previously reported metals in aqueous media. No reaction was observed with either manganese or copper alone as the mediator. Only a catalytic amount of copper is required for the proceeding of the reaction. The uses of Cu(0), Cu(I), and Cu(II) as the copper source are all effective. The use of a catalytic amount of manganese combined with a stoichoimetric amount of copper led to the failure of the reaction. Allyl chloride is found to be more effective than allyl bromide for the corresponding reaction. The use of substituted allyl halides gave a mixture of regio- and diastereoisomers. Aromatic aldehydes reacted chemoselectively in the presence of aliphatic aldehydes. An exclusive selectivity was also observed when both an aliphatic and an aromatic aldehyde functionalities are present in the same molecule. In the presence of acetic acid or ammonium chloride, manganese was found to effect the pinacol-coupling reaction in water. The reaction proceeds selectively with aryl aldehydes.