Palladium-catalyzed generation of O-allylic urethanes and carbonates from amines/alcohols, carbon dioxide, and allylic chlorides

McGhee, William D.; Riley, Dennis P.; Christ, M. E.; Christ, K.

doi:10.1021/om00028a069

Cited by 72 publications

(32 citation statements)

References 2 publications

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“…Most of the approaches rely on the generation of the carbamate anion via the reaction of carbon dioxide and amines, followed by the reaction with electrophiles, usually alkyl halides. 93 − 95 …”

Section: Methods For the Synthesis Of Carbamatesmentioning

confidence: 99%

Organic Carbamates in Drug Design and Medicinal Chemistry

2015

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The carbamate group is a key structural motif in many approved drugs and prodrugs. There is an increasing use of carbamates in medicinal chemistry and many carbamate derivatives are specifically designed to make drug-target interactions through their carbamate moiety. In this review, we present properties and stabilities of carbamates, reagents and chemical methodologies for the synthesis of carbamates, and recent application of carbamates in drug design and medicinal chemistry.

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Section: Methods For the Synthesis Of Carbamatesmentioning

confidence: 99%

Organic Carbamates in Drug Design and Medicinal Chemistry

2015

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“…137 Polyurethanes (11) have also been prepared by the reactions of dicarbamate ions formed by insertion of CO 2 into diamines, followed by Pd-catalyzed coupling to 1,4-dichloro-2-butene. 138 Reductive carboxylations in which the CO 2 unit is incorporated into the product are also known. In the case of alkynes and olefins, electrochemical reductive carboxylations result in effective addition of the formic acid C-H bond to C-C double or triple bonds.…”

Section: Chemicalsmentioning

confidence: 99%

Catalysis Research of Relevance to Carbon Management: Progress, Challenges, and Opportunities

et al. 2001

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“…The reactions of CO2 with amine-containing nucleophiles were studied (Scheme 14), mainly using precious-metal (Ag [120,121], Pd [122][123][124], and Ru [125,126] or organotin [127,128] (Sn)) catalysts, e.g., (a) oxazolidinones from aziridine [129], 1,2-aminoalcohols [127], and α-allenyl amines [124]; (b) benzoxazin-2-ones from o-alkynylanilines [120,121]; (c) carbamates from amine/allylic chloride [122,123], amine/alkyne [130], and N-substituted propargylamine [126]; and (d) urea or urethane from primary amine [128,131]. The carboxylation of carbon nucleophiles with CO2 was studied (Scheme 15), mainly with Cu [132,133], Ni [133][134][135][136][137][138][139], and Pd [140][141][142][143][144][145] catalysts, e.g., (a) substituted carboxylic acid from arylhalide [139,140], benzyl chloride [134], alkynes [135,136], allenes [122], and alkenes [132,146]; (b) ester from al...…”

Section: Horizontal Functionalization Of Co2mentioning

confidence: 99%

“…Examples of metal-catalyzed CO2 functionalization with amine-containing nucleophiles[120][121][122][123][124][125][126][127][128][129][130][131]. Examples of metal-catalyzed carboxylation of carbon nucleophiles with CO2.…”

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confidence: 99%

Molecular Catalysis for Utilizing CO2 in Fuel Electro-Generation and in Chemical Feedstock

Leung¹,

Ho²

2019

Catalysts

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Processes for the conversion of CO2 to valuable chemicals are highly desired as a result of the increasing CO2 levels in the atmosphere and the subsequent elevating global temperature. However, CO2 is thermodynamically and kinetically inert to transformation and, therefore, many efforts were made in the last few decades. Reformation/hydrogenation of CO2 is widely used as a means to access valuable products such as acetic acids, CH4, CH3OH, and CO. The electrochemical reduction of CO2 using hetero- and homogeneous catalysts recently attracted much attention. In particular, molecular CO2 reduction catalysts were widely studied using transition-metal complexes modified with various ligands to understand the relationship between various catalytic properties and the coordination spheres above the metal centers. Concurrently, the coupling of CO2 with various electrophiles under homogeneous conditions is also considered an important approach for recycling CO2 as a renewable C-1 substrate in the chemical industry. This review summarizes some recent advances in the conversion of CO2 into valuable chemicals with particular focus on the metal-catalyzed reductive conversion and functionalization of CO2.

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Palladium-catalyzed generation of O-allylic urethanes and carbonates from amines/alcohols, carbon dioxide, and allylic chlorides

Cited by 72 publications

References 2 publications

Organic Carbamates in Drug Design and Medicinal Chemistry

Organic Carbamates in Drug Design and Medicinal Chemistry

Catalysis Research of Relevance to Carbon Management: Progress, Challenges, and Opportunities

Molecular Catalysis for Utilizing CO2 in Fuel Electro-Generation and in Chemical Feedstock

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