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Upstream product

• 3350-78-5 3,3-Dimethylacryloyl chloride 
• 70-55-3 toluene-4-sulfonamide 
• 541-47-9 3-Methylbutenoic acid 
• 107-86-8 3,3-dimethyl acrylaldehyde 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 

Relevant academic research and scientific papers

Practical copper(I)-catalysed amidation of aldehydes

The direct synthesis of amides by insertion into the C-H bond of aldehydes is shown to be a practical procedure through application of cheap, readily available catalysts generated in situ from copper(i) halides and pyridine. The Royal Society of Chemistry 2010.

Iron(II)-catalyzed amidation of aldehydes with iminoiodinanes at room temperature and under microwave-assisted conditions

A method for the amidation of aldehydes with PhI=NTs/PhI=NNs as the nitrogen source and an inexpensive iron(II) chloride + pyridine as the in situ formed precatalyst under mild conditions at room temperature or microwave assisted conditions is described. The reaction was operationally straightforward and accomplished in moderate to excellent product yields (20-99%) and with complete chemoselectivity with the new C-N bond forming only at the formylic C-H bond in substrates containing other reactive functional groups. By utilizing microwave irradiation, comparable product yields and short reaction times of 1 h could be accomplished. The mechanism is suggested to involve insertion of a putative iron-nitrene/imido group to the formylic C-H bond of the substrate via a H-atom abstraction/radical rebound pathway mediated by the precatalyst [Fe(py)4Cl2] generated in situ from reaction of FeCl 2 with pyridine.

Highly efficient ruthenium(II) porphyrin catalyzed amidation of aldehydes

H to N: The first example of a mild, highly efficient C-H bond amidation catalyzed by ruthenium(II) porphyrin complexes uses PhI=NTs as the nitrogen source for installing the amide bond functionality in a wide variety of aldehydes (see scheme). The protocol is chemoselective, with the new C-N bond forming only at the acyl C-H bond, even in aldehyde substrates containing other functional groups.

4-endo-trig cyclization processes using bis(collidine)bromine(i) hexafluorophosphate as reagent: Preparation of 2-oxetanones, 2-azetidinones, and oxetanes

Reaction in methylene chloride of bis(collidine)bromine(I) hexafluorophosphate with α,β-unsaturated acids and α,β-unsaturated N- sulfonamides was found to lead diastereospecifically to the corresponding 2- oxetanones and 2-azetidinones in moderate yields (23-60%), by an almost unknown 4-endo cyclization. This process allow the synthesis of these interesting classes of products in one step from common substrates. Similarly, the reaction of cinnamic alcohols led, by the same cyclization procedure, to oxetanes (20-36%); the presence of a gem-dimethyl group in α of the alcohol function appeared beneficial.