Highly efficient methods for the one-pot synthesis of β-substituted enones

Abstract

A mild and practically-convenient one-pot procedure for the direct beta-substitution of enones has been developed using a conjugate addition-oxidation strategy with a full range of copper-based reagents and N-tert-butylphenylsulfinimidoyl chloride; alkyl- and aryl-substituted enones are delivered in good to excellent yields.

Recent Progress Toward Trifluoromethylselenolation Reactions

“…Weng, Chen, and coworkers proposed a mechanism for the trifluoromethylselenolation of β‐bromo enones, as shown in Scheme . The 1,4‐addition of [(bpy)Cu(SeCF 3 )] 2 to β‐bromo enone 21 afforded the intermediate A or B , which would generate the desired product 22 along with the departure of Cu(bpy)Br.…”

Synthesis of β-Trifluoromethylthio- and β-Trifluoromethylseleno-α,β-unsaturated Ketones through Copper-Mediated Trifluoromethylthio(seleno)lation

“…The 1,4-addition of LCu(SCF 3 ) 2a to β-bromo enone 1a provides the copper enolate complex I or II. [13][14][15] Subsequent bromide elimination would generate the desired trifluoromethylthiolated product 3a, along with LCuBr.…”

Copper/Selectfluor‐System‐Catalyzed Dehydration–Oxidation of Tertiary Cyclo­alcohols: Access to β‐Substituted Cyclohex‐2‐enones, 4‐Arylcoumarins, and Bi­aryls

“…Thus, a number of synthetic methods for the construction of this important unit have been developed in recent decades 6. Some representative methods include allylic oxidation of substituted cyclohexenes,6a–6d oxidative rearrangement of tertiary cyclohex‐2‐enols,6e–6i transition‐metal‐catalyzed oxidative Heck reactions2b,6j,6k and cross‐coupling reactions,6l and others 6m–6q. Although much progress has been made in this field, the development of new methods for the mild and efficient synthesis of β‐substituted cyclohex‐2‐enones from easily available starting materials is still in great demand.…”