β- and Z -selective metal-free cyanation of ynamides: a direct approach to piperidines fused to arenes

2026/01/01 by Dorian Schutz, Wenwen Yang, Laurence Miesch · 1 voice
Chemistry · #Catalytic Alkyne Reactions #Catalytic Cross-Coupling Reactions #Catalytic C–H Functionalization Methods

paper · pdf · doi:10.1039/d6qo00022c

openalex publication_date 2026/01/01 · openalex created_date 2026/02/25 · openalex updated_date 2026/07/22

Abstract

Stereodefined β-cyanoenamides were synthesized from ynamides using TMSCN/TBAF. Strategic nitrile activation with TMSOTf promoted intramolecular cyclization, delivering densely functionalized piperidines in a streamlined sequence.

Discussions

• Congratulations to Dorian Schutz and Wenwen Yang for this beautiful work in @orgchemfront.rsc.org Open Access ! doi.org/10.1039/D6QO... [bsky, 2 points, 0 comments]

Related

• The electrophilic cyanation of alkynyl halides (bromides or chlorides) with N-cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS) using a zinc reagent
• Interrupted intramolecular [3 + 2] to 5- endo-dig cyclization: [3 + 2] cycloaddition of nitrile ylides of diazo esters: photo-induced solvent-free gem -diamination to synthesize α-amino-α-substituted α-amino esters
• Direct Catalytic Deaminative Cyanation of Aliphatic Primary Amines
• Photoredox-Catalyzed Radical Cascade Cyclization of N -Cyanamide Alkenes with N -Aminopyridinium Salts: Modular Synthesis of Polycyclic Quinazolinones
• C−H Cyanation of 6‐Ring N‐Containing Heteroaromatics