Environmentally Friendly Protocol for the Oxidative Iodofunctionalization of Olefins in a Green Solvent

Yi, Wei; Wang, Pengfei; Lu, Meng; Liu, Qianqian; Bai, Xue; Chen, Kai-Die; Zhang, Jingwen; Liu, Gong‐Qing

doi:10.1021/acssuschemeng.9b04298

Cited by 17 publications

(7 citation statements)

References 100 publications

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“…Komatsu and co‐workers discovered a convenient synthesis of three to six‐membered N‐heterocycles from N ‐alkenyl amides utilizing t ‐BuOI [5] or I 2 [6] as oxidant and iodide sources. Other elegant strategies by employing different oxidants like PhI(OAc) 2 , [7] MnI 2 , [8] I 2 O 5 , [9] NBS, [10] CuBr 2 , [11] also have been established by various groups. In addition, palladium‐catalyzed intramolecular halo‐amination of alkene was reported by the groups of Liu [12] and Li [13] independently.…”

Section: Methodsmentioning

confidence: 99%

Practical Synthesis of Halogenated N‐Heterocycles via Electrochemical Anodic Oxidation of Unactivated Alkenes

Qin

et al. 2021

Eur J Org Chem

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A general and efficient intramolecular halo‐amination of unactivated alkenes for the synthesis of various halogenated N‐heterocycles was developed via electrochemical anodic oxidation. This protocol proceeds in a simple undivided cell by employing LiI or LiBr as redox mediums and halogen sources. A wide range of halogenated N‐heterocycles, including three‐, five‐, and six‐membered N‐heterocycles were constructed in moderate to good yields at room temperature. Notably, this electrochemical oxidative transformation avoids the utilization of external oxidants and strong bases, therefore represents an environmentally benign approach.

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Section: Methodsmentioning

confidence: 99%

Practical Synthesis of Halogenated N‐Heterocycles via Electrochemical Anodic Oxidation of Unactivated Alkenes

Qin

et al. 2021

Eur J Org Chem

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“…Similar heterocycles can be obtained using a chloramine-T/I 2 system. In addition, the Liu group recently reported an eco-friendly protocol based on an I 2 O 5 /LiI system ( Figure 40 b) [ 93 ]. The use of this method allows a reduction in the reaction time and leads to an improvement in the yield.…”

Section: Substrate-switchable Cyclizationsmentioning

confidence: 99%

Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy

et al. 2020

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In organic synthesis, due to their high electrophilicity and leaving group properties, halogens play pivotal roles in the activation and structural derivations of organic compounds. Recently, cyclizations induced by halogen groups that allow the production of diverse targets and the structural reorganization of organic molecules have attracted significant attention from synthetic chemists. Electrophilic halogen atoms activate unsaturated and saturated hydrocarbon moieties by generating halonium intermediates, followed by the attack of carbon-containing, nitrogen-containing, oxygen-containing, and sulfur-containing nucleophiles to give highly functionalized carbocycles and heterocycles. New transformations of halogenated organic molecules that can control the formation and stereoselectivity of the products, according to the difference in the size and number of halogen atoms, have recently been discovered. These unique cyclizations may possibly be used as efficient synthetic strategies with future advances. In this review, innovative reactions controlled by halogen groups are discussed as a new concept in the field of organic synthesis.

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“…Similar heterocycles can be obtained using a chloramine-T/I2 system. In addition, the Liu group recently reported an eco-friendly protocol based on an I2O5/LiI system (Figure 40b) [94]. The use of this method allows a reduction in the reaction time and leads to an improvement in the yield.…”

Section: O/n Atom-selective Cyclizationsmentioning

confidence: 99%

Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy

China

Kumar

Kikushima

et al. 2020

Preprint

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In organic synthesis, due to their high electrophilicity and leaving group properties, halogens play pivotal roles in the activation and structural derivations of organic compounds. Recently, cyclizations induced by halogen groups that allow the production of diverse targets and the structural reorganization of organic molecules have attracted significant attention from synthetic chemists. Electrophilic halogen atoms activate unsaturated and saturated hydrocarbon moieties via the generation of halonium intermediates, followed by the attack of carbon-, nitrogen-, oxygen-, and sulfur-containing nucleophiles to give highly functionalized carbo- and heterocycles. Interestingly, new transformations of halogenated organic molecules that can control the formation and stereoselectivity of the products according to the difference in the size and number of halogen atoms have recently been discovered. These unique cyclizations may possibly be used as efficient synthetic strategies with future advances. In this review, innovative reactions controlled by halogen groups are discussed as a new concept in the field of organic synthesis.

show abstract

Environmentally Friendly Protocol for the Oxidative Iodofunctionalization of Olefins in a Green Solvent

Cited by 17 publications

References 100 publications

Practical Synthesis of Halogenated N‐Heterocycles via Electrochemical Anodic Oxidation of Unactivated Alkenes

Practical Synthesis of Halogenated N‐Heterocycles via Electrochemical Anodic Oxidation of Unactivated Alkenes

Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy

Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy

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