278167-60-5

Upstream product

• 278167-19-4 1-(p-toluenesulfonyl)-3-trimethylsilyl-4-iodo-1H-pyrrole 
• 278167-52-5 1-(p-toluenesulfonyl)-3-trimethylsilyl-4-phenyl-1H-pyrrole 

Downstream Products

• 278167-59-2 1-(p-toluenesulfonyl)-3-phenyl-4-(trans-2-methoxycarbonylethenyl)-1H-pyrrole 
• 278167-61-6 1-(p-toluenesulfonyl)-3-(p-methoxyphenyl)-4-phenyl-1H-pyrrole 

Relevant academic research and scientific papers

CuI-Catalyzed Decarboxylative Thiolation of Propargylic Cyclic Carbonates/Carbamates to Access Allenyl Thioethers

The first CuI-catalyzed decarboxylative thiolation of terminal alkyne-substituted cyclic carbonates/carbamates to access allenes has been developed. A wide range of hydroxymethyl-and aminomethyl-containing allenyl thioethers were smoothly obtained in good to excellent yields under mild conditions. The copper-allenylidene intermediate among the process is crucial to the decarboxylative thiolation reaction. This method opens up a new channel to access allenyl thioether compounds.

Highly regioselective synthesis of 3,4-disubstituted 1H-pyrrole

A highly regioselective method for the synthesis of 3,4-disubstituted 1H-pyrroles has been developed employing the ipso-directing property of a trimethylsilyl group. As a key starting material in this study, the known 3,4-bis(trimethylsilyl)-1H-pyrrole (3), was protected with carefully chosen groups, namely tert-butoxycarbonyl, N,N-dimethylaminosulfonyl, p- toluenesulfonyl, and triisopropylsilyl. A highly regioselective monoiodination of these 1-protected pyrroles was achieved by reaction with iodine - silver trifluoroacetate at low temperatures. Subsequent palladium- catalyzed cross-coupling reactions afforded 1-protected-4-substituted 3- trimethylsilyl-1H-pyrroles, which again underwent further room-temperature ipso-iodination and palladium-catalyzed cross-coupling reactions to provide symmetrical and unsymmetrical 1-protected-3,4-disubstituted 1H-pyrroles. Deprotection of 1-(tert-butoxycarbonyl) and 1-(N,Y-dimethylaminosulfonyl) groups was found to be nontrivial. The 1-(p-toluenesulfonyl) protecting group was eventually proved to be superior to other protection groups, because it was readily removed after stepwise ipso monoiodinations and palladium- catalyzed cross-coupling reactions.