37940-38-8

Upstream product

• 501-65-5 diphenyl acetylene 
• 177750-12-8 N-{1-(4-bromophenyl)vinyl}acetamide 
• 16483-98-0 2,3-diphenyl-2H-azirine 
• 99-90-1 para-bromoacetophenone 
• 402727-63-3 tert-butyl N'-[1-(4-bromophenyl)ethylidene]hydrazinecarboxylate 
• 451-40-1 phenyl benzyl ketone 
• 89108-50-9 1-(1-azidovinyl)-4-bromobenzene 

Relevant academic research and scientific papers

Iron-Catalyzed Radical Cycloaddition of 2H-Azirines and Enamides for the Synthesis of Pyrroles

A novel and efficient Fe-catalyzed radical cycloaddition of 2H-azirines and enamides for the synthesis of substituted pyrroles has been developed. The radical cycloaddition reaction proceeded through a conceptually new Fe(II)-catalyzed homolytic cleavage of C-N bond of 2H-azirines sequential radical cyclization with enamides. The reaction used readily available starting materials, tolerated various functional groups, and afforded valuable triaryl-substituted pyrroles in good to high yields under mild reaction conditions.

Rhodium-Catalyzed Oxidative Cycloaddition of N-tert-Butoxycarbonylhydrazones with Alkynes for the Synthesis of Functionalized Pyrroles via C(sp3)–H Bond Functionalization

A rhodium(III)-catalyzed cycloaddition of N-tert-butoxycarbonylhydrazones with internal alkynes was developed. The reaction features a regioselective α-imino alkyl C(sp3)?H bond functionalization resulting in selective formation of highly functionalized NH-free pyrroles. Our studies showed that utilizing the N-tert-butoxycarbonyl (N-Boc) as the oxidizing directing group is critical for achieving the observed pyrrole formation versus the isoquinoline formation. To account for the pyrrole formation, we hypothesized that a prior tautomerization of the N-Boc-hydrazones to enamines should occur, followed by regioselective C(sp2)–H cleavage to form a putative five-membered rhodacycle. Subsequent coupling of the rhodacycle with the alkynes would afford the pyrrole products. (Figure presented.).

Copper-catalyzed C(sp3)-H functionalization of ketones with vinyl azides: synthesis of substituted-1H-pyrroles

Copper-catalyzed C(sp3)-H functionalization of ketones with vinyl azides for the synthesis of substituted pyrroles has been developed. The method is a straightforward and efficient way to access a series of 2,3,5-trisubstituted-1H-pyrroles in modest to excellent yields with broad functional group tolerance under mild conditions.

Synthesis of multi-substituted pyrroles using enamides and alkynes catalyzed by Pd(OAc)2 with molecular oxygen as an oxidant

A cyclization reaction between enamides and alkynes catalyzed by palladium(ii) acetate is described. In this method, the molecular oxygen serves as an efficient oxidant for the Pd(ii)/Pd(0) catalytic cycle. The simple reaction conditions permit this methodology to be used as a general tool for the preparation of multi-substituted pyrroles.