Iodine-promoted transfer of dihydrogen from ketones to alkenes, triphenylmethyl, and diphenylmethyl derivatives

Duan, Yiping; Zhong, Wenyi; Zeng, Zhaolan; Feng, Jiajie; Xu, Jinyi; Yang, Fulai; Liu, Jie

doi:10.1039/d3cc03409g

Cited by 2 publications

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“…It is noteworthy that, despite the fact that the trityl group is a widely used protective group for amines, direct trityl amine deamination is scarce and requires a large excess of alkali metal on silica gel, or iodine (I 2 ) to activate the -NH 2 . Similar to that of the trityl amine, the reaction between 1 and diphenylmethyl amine (Ph 2 CHNH 2 ) produces corresponding deamination product [Na(2,2,2-cryptand)][Ph 2 CH] ( 3 ) (Figure b).…”

Section: Resultsmentioning

confidence: 99%

Mechanochemical Synthesis of a Sodium Anion Complex [Na⁺(2,2,2-cryptand)Na^–] and Studies of Its Reactivity: Two-Electron and One-Electron Reductions

Davison,

Hemingway,

Wills

et al. 2024

Inorg. Chem.

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Group 1 metal molecular chemistry is dominated by a +1 oxidation state, while a 0 oxidation state is widespread in the metals. A more exotic, yet still available, oxidation state of group 1 metal is −1, i.e., alkalide. Reported as early as the 1970s, the alkalides appear in every modern inorganic chemistry textbook as an iconic chemical curiosity, yet their reactivity remains unexplored. This is due to their synthetic hurdles. In this work, we report the first facile synthesis of the archetypical alkalide complex, [Na + (2,2,2-cryptand)Na − ], which allows us to unveil a versatile reactivity profile of this once exotic species.

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Section: Resultsmentioning

confidence: 99%

Mechanochemical Synthesis of a Sodium Anion Complex [Na⁺(2,2,2-cryptand)Na^–] and Studies of Its Reactivity: Two-Electron and One-Electron Reductions

Davison,

Hemingway,

Wills

et al. 2024

Inorg. Chem.

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Iodine-Promoted Reductive Sulfenylation Using Ketones as Hydride Donors

Duan,

Guo,

Zheng

et al. 2024

J. Org. Chem.

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Herein, an iodine-promoted reductive sulfenylation reaction of ketones with disulfides has been developed. This method provides an approach for synthesizing unsymmetrical alkyl−alkyl and alkyl−aryl sulfides in a single step. Investigation of the reaction mechanism revealed that ketones play a dual role in this process. They react with disulfides to produce vinyl thioethers and act as effective organic hydride donors, reducing the number of vinyl thioethers that are formed in situ. This study expands the range of applications of ketones in chemical synthesis.

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Iodine-promoted transfer of dihydrogen from ketones to alkenes, triphenylmethyl, and diphenylmethyl derivatives

Abstract: Herein, a novel class of transfer hydrogenation agent, cycloheptanone, has been successfully employed in metal-free hydrogenation facilitated by iodine. A series of alkenes, triphenylmethyl derivatives, and diphenylmethyl derivatives were reduced...

Cited by 2 publications

References 61 publications

Mechanochemical Synthesis of a Sodium Anion Complex [Na⁺(2,2,2-cryptand)Na^–] and Studies of Its Reactivity: Two-Electron and One-Electron Reductions

Mechanochemical Synthesis of a Sodium Anion Complex [Na⁺(2,2,2-cryptand)Na^–] and Studies of Its Reactivity: Two-Electron and One-Electron Reductions

Iodine-Promoted Reductive Sulfenylation Using Ketones as Hydride Donors

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Iodine-promoted transfer of dihydrogen from ketones to alkenes, triphenylmethyl, and diphenylmethyl derivatives

Abstract: Herein, a novel class of transfer hydrogenation agent, cycloheptanone, has been successfully employed in metal-free hydrogenation facilitated by iodine. A series of alkenes, triphenylmethyl derivatives, and diphenylmethyl derivatives were reduced...

Cited by 2 publications

References 61 publications

Mechanochemical Synthesis of a Sodium Anion Complex [Na+(2,2,2-cryptand)Na–] and Studies of Its Reactivity: Two-Electron and One-Electron Reductions

Mechanochemical Synthesis of a Sodium Anion Complex [Na+(2,2,2-cryptand)Na–] and Studies of Its Reactivity: Two-Electron and One-Electron Reductions

Iodine-Promoted Reductive Sulfenylation Using Ketones as Hydride Donors

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Mechanochemical Synthesis of a Sodium Anion Complex [Na⁺(2,2,2-cryptand)Na^–] and Studies of Its Reactivity: Two-Electron and One-Electron Reductions

Mechanochemical Synthesis of a Sodium Anion Complex [Na⁺(2,2,2-cryptand)Na^–] and Studies of Its Reactivity: Two-Electron and One-Electron Reductions