Synthesis based on electrogenerated carbenes Communication 1. Some reactions with the participation of dichlorocarbene

Photons or Electrons? A Critical Comparison of Electrochemistry and Photoredox Catalysis for Organic Synthesis

“…1071 A route to gem-dichlorocyclopropanes following a similar strategy has been reported by Petrosyan and co-workers using CCl 4 and alkenes in chloroform containing tetraalkylammonium electrolyte in a divided cell using a lead cathode. 1072 A synthetically useful electrochemical analog to the Simmons−Smith reaction was first shown by Peŕichon and co-workers, who reported the synthesis of cyclopropanes via dihalomethane reduction in the presence of alkenes within an undivided cell. 1073 The results suggest in situ formation of a zinc carbenoid (CH 2 ZnI 2 ), an intermediate observed in the Simmons−Smith reaction.…”

“…Another strategy for electrolytic substrate activation is to generate stabilized carbenes (e.g., dihalocarbene); this was accomplished on a preparative scale by Fritz and Kornrumpf, − as well as Baizer and Chruma . A route to gem -dichlorocyclopropanes following a similar strategy has been reported by Petrosyan and co-workers using CCl 4 and alkenes in chloroform containing tetraalkylammonium electrolyte in a divided cell using a lead cathode . A synthetically useful electrochemical analog to the Simmons–Smith reaction was first shown by Périchon and co-workers, who reported the synthesis of cyclopropanes via dihalomethane reduction in the presence of alkenes within an undivided cell .…”

Electrochemical synthesis of cyclopropanes

“…The electrolysis was carried out in the cathode compartment of a divided electrolytic cell equipped with a lead cathode and a platinum anode at a constant current of 0.2 A for 3 ± 6 h. The current efficiency for cyclopropane 15a ± c was 13% ± 45% (Scheme 11, the chemical yields are shown). 23 The nucleophilic addition of organic anions to the activated double bond in the presence of bases, i.e., the Michael reaction, 6, 7 is a fundamental method for the formation of carbon ± carbon bonds in classical organic chemistry. For the synthesis of functionally substituted cyclopropanes, a version of the Michael reaction with the subsequent closure of a three-membered ring was used.…”