Indium-catalyzed Reduction of a Nitroarene Using a Hydrosilane: A Selective Reduction Strategy for the Efficient Synthesis of Indoprofen

Ogiwara, Yohei; Sakurai, Yuka; Sakai, Norio

doi:10.1246/cl.161008

Cited by 6 publications

(2 citation statements)

References 39 publications

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“…In the case of cinnamic acids 92 , both enamine and allylic amine products were observed. Similar to previous observations, [23] the existence of nitro groups and esters was not well tolerated, due to the occurrence of competing reduction reactions. Mechanistic studies reveal that the initial step involved the generation of silyl ester intermediates 96 through a base‐catalyzed dehydrogenative process.…”

Section: Catalytic Reactionssupporting

confidence: 89%

“…Sakai and coworkers also achieved the total synthesis of indoprofen, employing In(OAc) 3 -catalyzed and hydrosilanebased reductive lactamization from 2-formylbenzoic acid. [23] Additionally, a highly efficient single-atom cobalt catalyst for the transformation of β-keto acids 80 to lactams 83 (n = 1) was developed by Liu, Beller, Jagadeesh, and coworkers, using hydrogen gas (20 bar) as the reducing agent. Their work offered an alternative approach to indoprofen.…”

Section: Hydrosilanes As Reducing Agentmentioning

confidence: 99%

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Catalytic One‐Pot Reductive Amination of Carboxylic Acids

Dong,

Yang

2024

ChemCatChem

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The broad applications of primary alkyl amines in various fields have spurred extensive interests in synthetic organic chemistry. Recently, the reductive amination of carboxylic acids has become an attractive and practical strategy for synthesizing primary alkyl amines, due to their wide availability and bench stability. However, the inherent stability and higher oxidation state of carboxylic acids render this new strategy with new challenges. This Concept provides a summary of the recent advancements in the reductive aminations of carboxylic acids, specifically focusing on the catalytic tactics, underlying mechanisms, and applications in the synthesis of valuable products.

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Section: Catalytic Reactionssupporting

confidence: 89%

Section: Hydrosilanes As Reducing Agentmentioning

confidence: 99%

Catalytic One‐Pot Reductive Amination of Carboxylic Acids

Dong,

Yang

2024

ChemCatChem

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Indium‐Catalyzed Deoxygenation of Sulfoxides with Hydrosilanes

2021

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Described herein is that a novel InBr 3 /PhSiH 3 reducing system in a 1,4-dioxane solution smoothly and effectively undertook deoxygenation of a variety of sulfoxides leading to the facile preparation of sulfide derivatives. Also, it was demonstrated that the reducing system shows a higher reactivity towards sulfoxides than that towards commonly reducible functional groups, such as carboxylic acids, esters, amides, and sulfones.

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