71777-97-4

Upstream product

• 188290-36-0 thiophene 
• 930-68-7 cyclohexenone 
• 45438-80-0 2-thienylzinc bromide 
• 1896-62-4 (E)-benzalacetone 
• 5590-45-4 (2-thienyl)copper 
• 6165-69-1 Thien-3-ylboronic acid 
• 193978-23-3 2-thiopheneboronic acid pinacol ester 

Relevant academic research and scientific papers

Palladium-Catalyzed Controllable Reductive/Oxidative Heck Coupling between Cyclic Enones and Thiophenes via C-H Activation

Herein, we report a straightforward, environmentally friendly, and controllable palladium/ligand catalytic system to enable reductive/oxidative Heck reactions of cyclic enones with thiophene or furan derivatives via C-H activation. The key to this tunable reaction is the appropriate intercepting thienyl-Pd(II)-enolate during the enolization process. Such a controllable and economic protocol would not only provide efficient methods to construct various value-added β-heteroarylated cyclic ketones/enones but also shed light on developing other conjugate addition reactions via C-H activation.

A consecutive process for C-C and C-N bond formation with high enantio-and diastereo-control: Direct reductive amination of chiral ketones using hydrogenation catalysts

High diastereoselectivity was observed in the Rh-catalysed reductive amination of 3-arylcyclohexanones to form tertiary amines. This was incorporated into a one-pot enantioselective conjugate addition and diastereoselective reductive amination, including an example of assisted tandem catalysis.

Heteroarylboronates in rhodium-catalyzed 1,4-addition to enones

Rhodium(I)-catalyzed 1,4-addition of aryl and alkenylboronic acids to α,β-unsaturated carbonyl compounds is well established, but the transfer of heteroaryl residues in this reaction remains underdeveloped. We have studied heteroaryl MIDA and pinacol boro

Enantioselective rhodium-catalysed 1,4-additions of 2-heteroarylzinc donors using Me-DUPHOS

The enantioselective 1,4-addition of 2-(substituted)thienylzinc and 2-furanylzinc reagents has been achieved (up to 99: 1 er) using a complex derived from [Rh(C2H4)2Cl]2 and Me-DUPHOS. The Royal Society of Chemistry.

Conjugate Michael additions with mixed diorganozincs

Functionalised mixed alkyl(trimethylsilylmethyl)zinc reagents add efficiently to a wide variety of Michael acceptors in high yield and with exclusive 1,4-regioselectivity, without the need for transition metal catalysis. The trimethylsilylmethyl group behaves as a non-transferable group, and in no cases was transfer of this group observed.

The Direct Formation of Functionalized Alkyl(aryl)zinc Halides by Oxidative Addition of Highly Reactive Zinc with Organic Halides and Their Reactions with Acid Chlorides, α,β-Unsaturated Ketones, and Allylic, Aryl, and Vinyl Halides

Highly reactive zinc, prepared by the lithium naphthalenide reduction of ZnCl2, readily undergoes oxidative addition to alkyl, aryl, and vinyl halides under mild conditions to generate the corresponding organozinc compounds in excellent yields.Significantly, the reaction will tolerate a spectrum of functional groups on the organic halides.Accordingly, this approach can now be used to prepare a wide variety of highly functionalized organozinc compounds.In the presence of Cu(I) salts, the organozinc compounds cross-couple with acid chlorides, conjugatively add to α,β-unsaturated ketones, and regioselectively undergo SN2' substitution reactions with allylic halides.They also cross-couple with aryl or vinyl halides with Pd(0) catalysts.

CHLORO- AND IODOTRIMETHYLSILANE-ACTIVATED ADDITIONS OF ORGANOCOPPER COMPOUNDS TO ENONES AND ENOATES

Organocopper compounds add to enones and enoates in the presence of chloromethylsilane in ether giving the conjugate adducts in preparatively usefu yields via the silyl enol ethers.Presence of lithium iodide is important and excess of chlorotrimethylsilane accelerates the reactions.The combination of organocopper compound, iodotrimethylsilane and dimethyl sulfide gave faster reactions and very high yields, particularly in dichloromethane, where the reaction mixtures gradually became homogeneous.

2-Thienyl as Auxiliary Group in Mixed Lithium Diorganocuprate

2-Thienylcopper (ThCu) gives mixed lithium organothienylcuprate reagents (LiRThCu) with organolithium compounds (R = methyl, butyl, phenyl and 2-pyridyl) in ether.These cuprates react with enones or enoates adding the group R, 1,4 to the substrates, 2-thienylcopper being regenerated.The isolated yields of conjugate addition are substantial (40-89percent) and comparable to those obtained with LiR2Cu in corresponding addition.Since a mixed organothienylcuprates are rather stable at 0 deg C, and sometimes even at room temperature, the 2-thienyl group is an useful auxiliary in mixed lithium organocuprates for conjugate addition.Lithium bis(2-thienyl)cuprate, on the other hand, gives 1,2- as well as 1,4-addition of the 2-thienyl group to enones and to methyl crotonate.