910896-12-7

Upstream product

• 51608-60-7 N-(benzylidene)-p-methylbenzenesulfonamide 
• 1296868-24-0 4-nitrobut-1-yne 
• 100-52-7 benzaldehyde 
• 70-55-3 toluene-4-sulfonamide 
• 1610764-09-4 C₁₈H₁₉NO₃S 
• 285565-39-1 4-methyl-N-(1-phenylbut-3-yn-1-yl)benzenesulfonamide 

Downstream Products

• 3042-21-5 2-methyl-5-phenyl-1H-pyrrole 

Relevant academic research and scientific papers

Gold(I)-promoted heterocyclization of internal alkynes: A comparative study of direct metallate 5-endo-dig cyclization versus a stepwise cyclization

With cationic gold catalysts, internal alkynes bearing both propargylic acyloxy groups and tosylamide pronucleophiles were found to cyclize to give either five- or six-membered ring nitrogen heterocycles. A wide variety of gold catalysts, counterions, and solvents were examined to elucidate their effect on product distribution. In most cases, the direct 5-endo-dig cyclization was found to be the major pathway leading to good yields of dehydropyrrolidine products. Alkyne substrates bearing additional normal alkyl substituents at the propargylic position gave dehydropiperidines as the major product. This pathway is thought to proceed by way of a 1,2- Rautenstrauch rearrangement to produce a vinyl gold(I) carbene, which undergoes conjugate addition by the nitrogen pronucleophile. Structural and electronic factors were studied in the nitrogen pronucleophile and in the migrating acyloxy group. Each was found to have a minor effect on the product ratio.

One-pot nitro-Mannich/hydroamination cascades for the direct synthesis of 2,5-disubstituted pyrroles using base and gold catalysis

An efficient, easy to perform, one-pot reaction cascade for the synthesis of 2,5-disubstituted pyrroles from p-toluenesulfonyl protected imines and 4-nitrobut-1-yne under a combination of base and gold(iii) catalysis is reported.

METHODS FOR THE SYNTHESIS OF HETEROAROMATIC COMPOUNDS

Methods of making heteroaromatic compounds comprising a 5- membered ring, and dihydro forms thereof, by a metal catalysed 5-endo-cyclisation of alkynes (acetylenes) are disclosed. The methods involve the use of a catalyst comprising a silver salt, more preferably a silver (I) salt, which is employed as a heterogeneous catalyst for the cyclisation reaction. The methods can produce different types of heteroaromatic compounds and are capable of producing highly substituted products, i.e. products in which the 5-membered ring is disubstituted, trisubstituted or, with further simple reactions, tetrasubstituted. The methods described herein generally the advantages that they use conditions and reagents that are benign, cheap and flexible and amenable to scale up, and in which the only by-product is water.