Microreactor mediated deoxygenation of benzylic alcohols in a biphasic organic-aqueous medium

Seo, Seung Woo; Song, Hyun Seung; Song, Ju Ha; Kim, Geon-Hee; In, Insik; Park, Chan Pil

doi:10.1016/j.tetlet.2015.04.039

Cited by 4 publications

(1 citation statement)

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“…Another biphasic method for the recovery of iodine species derived from the reduction of benzylic alcohols using the reagents HI and H 3 PO 2 was proposed by Park et al using a droplet-based microreactor. [58] This method minimizes operational risk by avoiding exposure to strongly acidic HI at high temperatures. It also optimizes the contact between hydrophilic reagents (HI and H 3 PO 2 ) and hydrophobic alcohols.…”

Section: Reduction Of Cà O Bondsmentioning

confidence: 99%

Iodine and Iodide in Reductive Transformations

2023

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This review provides a comprehensive overview of strategies and methodologies for reducing CÀ O and heteroatomicÀ oxygen bonds (NÀ O, SÀ O, PÀ O) using I 2 /I À , as well as other synthetically relevant bonds such as CÀ C, NÀ N, CÀ N, CÀ X, CÀ S. It highlights and discusses most of the mechanistic details provided by the original authors. Selected examples of other halides (Br and Cl) as reductants are also covered.

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Section: Reduction Of Cà O Bondsmentioning

confidence: 99%

Iodine and Iodide in Reductive Transformations

2023

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ChemInform Abstract: Microreactor Mediated Deoxygenation of Benzylic Alcohols in a Biphasic Organic‐Aqueous Medium.

Seo

Song

et al. 2015

ChemInform

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Iridium-Catalyzed Highly Efficient and Site-Selective Deoxygenation of Alcohols

et al. 2018

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An iridium-catalyzed, highly efficient, and site-selective deoxygenation of primary, secondary, and tertiary alcohols has been realized, under the assistance of a 4-(N-substituted amino)aryl directing group. Only the hydroxyl adjacent to the directing group can be deoxygenated. The deoxygenation is performed in water, with formic acid as both the promoter and hydride donor. Excellent yields and functionality tolerance, as well as high efficiency (S/C up to 1 000 000, TOF up to 445 000 h–1), are obtained. The kinetic isotope effect studies show that hydride formation is the rate-determining step, and the deoxygenation follows an S N 1-type pathway. The deoxygenation protocol has been demonstrated useful in the structural modification of naturally occurring ketones and steroids.

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Microreactor mediated deoxygenation of benzylic alcohols in a biphasic organic-aqueous medium

Cited by 4 publications

References 30 publications

Iodine and Iodide in Reductive Transformations

Iodine and Iodide in Reductive Transformations

ChemInform Abstract: Microreactor Mediated Deoxygenation of Benzylic Alcohols in a Biphasic Organic‐Aqueous Medium.

Iridium-Catalyzed Highly Efficient and Site-Selective Deoxygenation of Alcohols

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