Lewis Base Catalyzed Dioxygenation of Olefins with Hypervalent Iodine Reagents

Abstract

1,2-Diols are extremely useful building blocks in organic synthesis. Hypervalent iodine reagents are useful for the vicinal dihydroxylation of olefins to give 1,2-diols under metal-free conditions, but strongly acidic promoters are often required. Herein, we report a catalytic vicinal dioxygenation of olefins with hypervalent iodine reagents using Lewis bases as catalysts. The conditions are mild and compatible with various functional groups.

A Short and Facile [2 + 2] Photocycloaddition Protocol Toward Construction of a Levuglandin Skeleton

“…In the literature, numerous methods for the oxidation of olefins using various reagents have been reported. [18][19][20][21][22][23][24][25] We chose potassium permanganate in THF-water for the vicinal dihydroxylation of 11 as reported by Simandi and colleagues. 26,27 Thus the mixture of cyclobutenes 11 and 14 was treated with potassium permanganate in THF-water at room temperature.…”

Phenyliodine bis(trifluoroacetate) as a sustainable reagent: exploring its significance in organic synthesis

“…Numerous effective methods have been developed and are extensively utilized in contemporary chemistry. 151 Pan et al 152 have introduced a catalytic method for accomplishing the vicinal dioxygenation of olefins 179 (Scheme 74). They employed hypervalent iodine reagents with Lewis bases as catalysts.…”

“…Pan et al 152 have introduced a catalytic method for accomplishing the vicinal dioxygenation of olefins 179 (Scheme 74). They employed hypervalent iodine reagents with Lewis bases as catalysts.…”

Room-temperature tandem conversion of cyclic alkenes into 1,2-diols using molecular oxygen and β-MnO2 heterogeneous catalyst

“…1,2-Diols are an important class of organic intermediates for producing chemical products, such as antifreezes and medicines, polyester resins, and cosmetics. [1][2][3] Generally, the synthesis of 1,2-diols requires a two-step reaction process, including an alkene epoxidation reaction and an epoxide hydration reaction. For the alkene epoxidation reaction, an alkene is catalyzed by a catalyst in the presence of an oxidant and transformed into the corresponding epoxide.…”