<scp>C</scp>lemmensen Reduction of Ketones in Anhydrous Organic Solvents

Vedejs, E.

doi:10.1002/0471264180.or022.03

Cited by 2 publications

(1 citation statement)

References 35 publications

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“…Clemmensen reduction has historically been considered an important reaction. However, it is performed under harsh conditions, which include the use of concentrated HCl and toxic mercury.…”

Section: Introductionmentioning

confidence: 99%

A Simple Demonstration of Deoxygenation of Carbonyl Groups for Undergraduates in an Organic Chemistry Laboratory Class through Project-Based Learning

Liu,

Yan,

Lan

et al. 2023

J. Chem. Educ.

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The Clemmensen reduction is a common example of a reaction demonstrating the deoxygenation of carbonyl groups, which is a topic that has been widely studied in the field of organic chemistry. The use of trimethylchlorosilane, as a substitute for concentrated hydrochloric acid, allows for the reduction of carbonyl groups. The Clemmensen reduction experiment is performed by undergraduates for project-based learning. As a part of this program, students evaluate the influence of active functional groups, electron-donating and electron-withdrawing groups, steric hindrance, and other factors on the modified Clemmensen reduction using different reaction substrates. This lab activity aims to show the effectiveness of teaching organic chemistry laboratory methodologies to undergraduate students and serves as a tool for the final evaluation of practical knowledge using experiments. Project-based learning not only effectively improves the experimental ability of organic chemistry students but also has great importance in the development of interpersonal skills, including teamwork and innovative thinking. This helps to achieve the integration of appliedproject-based learning and organic chemistry experimental teaching objectives.

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“…Clemmensen reduction has historically been considered an important reaction. However, it is performed under harsh conditions, which include the use of concentrated HCl and toxic mercury.…”

Section: Introductionmentioning

confidence: 99%

A Simple Demonstration of Deoxygenation of Carbonyl Groups for Undergraduates in an Organic Chemistry Laboratory Class through Project-Based Learning

Liu,

Yan,

Lan

et al. 2023

J. Chem. Educ.

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Rhodium-Catalyzed Regioselective and Chemoselective Deoxygenative Reduction of 1,3-Diketones

et al. 2022

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The deoxygenative reduction of carbonyl compounds has been well established. However, most protocols developed typically require harsh reaction conditions or highly reactive/toxic reagents, and the deoxygenative reduction of 1,3-diketones is rarely explored despite their importance to synthetic chemistry and materials science. We describe here a rhodium-catalyzed regioselective and chemoselective deoxygenative reduction of 1,3-diketones under mild reaction conditions. This approach exhibited exceptionally high regioselectivity toward the aliphatic carbonyl reduction over aromatic carbonyl reduction. Moreover, the reaction showed good functional group tolerance and broad substrate scope as well as great potential in the late-stage modification and synthesis of natural products and pharmaceutical skeletons. Preliminary mechanistic studies and DFT calculations revealed that this reaction involved the deoxygenation of 1,3-diketone to α, β-unsaturated ketone and its subsequent 1,4-reduction. The noticeably lower energy barrier of the aliphatic CO insertion into [Rh]-Bpin versus the aromatic CO insertion was responsible for the high regioselectivity in this reduction.

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Clemmensen Reduction of Ketones in Anhydrous Organic Solvents

Cited by 2 publications

References 35 publications

A Simple Demonstration of Deoxygenation of Carbonyl Groups for Undergraduates in an Organic Chemistry Laboratory Class through Project-Based Learning

A Simple Demonstration of Deoxygenation of Carbonyl Groups for Undergraduates in an Organic Chemistry Laboratory Class through Project-Based Learning

Rhodium-Catalyzed Regioselective and Chemoselective Deoxygenative Reduction of 1,3-Diketones

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