Acid‐Catalyzed Carbene Transfer from Diazo Compounds: Carbocation versus Carbene as Key Intermediate

• Published in: European journal of organic chemistry Vol. 2022; no. 17
• Main Authors: Qu, Zheng‐Wang, Zhu, Hui, Grimme, Stefan
• Format: Journal Article
• Language: English
• Published: Weinheim Wiley Subscription Services, Inc 06.05.2022
• Subjects: Carbenes; Carbocations; Diazo compounds; Electrophilic substitution; Protonation; Reaction mechanisms; Substrates

An efficient mechanism for the acid‐catalyzed formal carbene transfer from diazo compounds to nucleophilic substrates is disclosed by DFT calculations. In sharp contrast to recent proposal via neutral carbene‐like intermediates, the new mechanism involves selective diazo C‐protonation to form cataly...