Iron(III)/O₂-Mediated Regioselective Oxidative Cleavage of 1-Arylbutadienes to Cinnamaldehydes

Abstract

A simple, efficient, and environmentally benevolent regioselective oxidative cleavage of 1-arylbutadienes to cinnamaldehydes mediated by iron­(III) sulfate/O2 has been developed. The reaction offered good yields and excellent regioselectivity and showed good functional group tolerance (31 examples). The method is important, as few reports with limited substrate scope are available for such excellent oxidative cleavage of conjugated dienes.

Phosphorus-Recycling Wittig Reaction: Design and Facile Synthesis of a Fluorous Phosphine and Its Reusable Process in the Wittig Reaction

“…[ E -Isomer (CAS no. 37985-13-0)]: 1 H NMR (400 MHz, CDCl 3 ) δ 7.43 (d, J = 7.8 Hz, 2H), 7.22–7.36 (m, 7H), 6.87–6.96 (m, 2H), 6.55–6.72 (m, 2H); 13 C­{ 1 H} NMR (100 MHz, CDCl 3 ) δ 137.3, 136.0, 133.5, 133.2, 131.5, 129.9, 129.0, 128.9, 128.8, 127.8, 127.6, 126.5.…”

Oxidative Cleavage of Alkenes by O2 with a Non-Heme Manganese Catalyst

“…In response to the mounting environmental and safety issues, the past four decades have witnessed the study of numerous transition metal catalysts for oxidative cleavage of alkenes (Scheme c,d). ,, More recently, organo- and photocatalytic methods have been put forward. , Although various mild oxidants have been examined, the use of O 2 remains of utmost interest, as it is the most easily available, least expensive, and cleanest oxidant. Pleasingly, a number of the reported methods now allow O 2 to be used as the oxidant under various conditions. , Notwithstanding the progress made, almost all the methods reported so far can only deal with activated alkenes, such as styrene and derivatives. In particular, until now, there appear to be no known catalysts that can be used to cleave the more spread, nonactivated aliphatic alkenes by using atmospheric O 2 , while showing a substrate scope of potential for organic synthesis .…”

Oxidative cleavage of C–C double bond in cinnamic acids with hydrogen peroxide catalysed by vanadium(v) oxide

“…The aerobic oxidative cleavage of carbon-carbon double bonds is very promising; however, improvements are still needed to compete with conventional oxidants. [18][19][20][21][22][23][24] Hydrogen peroxide is similar to oxygen in that water is the only by-product, while the reactions can be carried out in a homogeneous phase. [25][26][27] The use of H 2 O 2 for the oxidative cleavage of olefins has been described in several articles, however there is a lack of simple and costeffective methods.…”