A copper-catalyzed oxidative coupling reaction of arylboronic acids, amines and carbon dioxide using molecular oxygen as the oxidant

Xiong, Wenfang; Qi, Chaorong; Guo, Tianzuo; Zhang, Min; Chen, Kai; Jiang, Huanfeng

doi:10.1039/c6gc03465a

Cited by 44 publications

(21 citation statements)

References 55 publications

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“…In this particular system, CO2 works as a co-catalyst in association with the ruthenium complex, generating a carbamate as a reaction intermediate (Scheme 37) [270]. In addition to the above mentioned reactions, Jiang et al reported the involvement of Cu(II) and Cu(III) carbamates in the oxidative coupling of arylboronic acids [322] and in the cyclization of enynes [323] from amines and CO2. In order to support the hypothesis of an in situ formed Cu(II) carbamate, the catalytic activity of [Cu(O2CNBn)2(NHBn2)2] was evaluated, providing moderate to good results in term of product yields.…”

Section: Co 2 Activation Routesmentioning

confidence: 99%

Recent Advances in the Chemistry of Metal Carbamates

et al. 2020

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Following a related review dating back to 2003, the present review discusses in detail the various synthetic, structural and reactivity aspects of metal species containing one or more carbamato ligands, representing a large family of compounds across all the periodic table. A preliminary overview is provided on the reactivity of carbon dioxide with amines, and emphasis is given to recent findings concerning applications in various fields.

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Section: Co 2 Activation Routesmentioning

confidence: 99%

Recent Advances in the Chemistry of Metal Carbamates

et al. 2020

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“…In 2017, Jiang’s group developed a novel copper-promoted oxidative coupling reaction of arylboronic acids, amines and CO 2 (Scheme ). In this example, the initially added Cu 2 O can be oxidized into Cu(II) complex A in the presence of O 2 , amine, and CO 2 . After that, A undergoes coordination exchange with pyridine facilitated by BF 3 ·Et 2 O, generating intermediate B .…”

Section: Miscellaneous C–cu Bond Formation For Co2 Conversionmentioning

confidence: 99%

“…In 2017, Jiang's group developed a novel copper-promoted oxidative coupling reaction of arylboronic acids, amines and CO 2 (Scheme 33). 81…”

Section: ■ C−cu Bond Formation By Transmetalationmentioning

confidence: 99%

Construction of C–Cu Bond: A Useful Strategy in CO₂ Conversion

2019

Organometallics

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Carbon dioxide is not only one of the greenhouse gases but also an appealing renewable C 1 source. To reconcile the environmental benefit with chemical industry development, conversion of CO 2 into valuable chemicals is proposed, and tremendous effort has been devoted to developing new synthetic protocols and highly efficient catalytic systems, wherein copper catalysis is attractive and features effective, inexpensive, and diverse transformation of CO 2 . Considering the ubiquity of the C−Cu bond in organic chemistry and the wide application of the resulting carbocuprate species in reductive coupling with electrophiles, C−Cu formation and subsequent CO 2 insertion has been developed as an important strategy for CO 2 chemical fixation, thereby resulting in the preparation of a variety of valuable chemicals. To arouse broad interest in this strategy, we summarize recent advances and give an overview on CO 2 transformations via the carbocuprate species on the basis of the C−Cu bond formation mechanism, including copper-promoted alkyne and halide activation, transmetalation of some specific chemicals with copper, and hydrocupration, borocupration, and silylcupration of unsaturated substrates. It is hoped that this review can provide some clues for further exploration in this field.

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“…Additionally, a more convenient route to O -aryl carbamates by a copper(I)-catalyzed oxidative coupling reaction between arylboronic acids, amines and CO 2 was developed (Scheme 18b) [103]. At the same time, BF 3 ·OEt 2 was employed as the promoter and O 2 as the oxidant.…”

Section: Chemical Fixation Of Co2 Through C-n Bond Formationmentioning

confidence: 99%

Catalytic Conversion of Carbon Dioxide through C-N Bond Formation

Song

Zhang

et al. 2019

Molecules

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From the viewpoint of green chemistry and sustainable development, it is of great significance to synthesize chemicals from CO2 as C1 source through C-N bond formation. During the past several decade years, many studies on C-N bond formation reaction were involved, and many efforts have been made on the theory. Nevertheless, several great challenges such as thermodynamic limitation, low catalytic efficiency and selectivity, and high pressure etc. are still suffered. Herein, recent advances are highlighted on the development of catalytic methods for chemical fixation of CO2 to various chemicals through C-N bond formation. Meanwhile, the catalytic systems (metal and metal-free catalysis), strategies and catalytic mechanism are summarized and discussed in detail. Besides, this review also covers some novel synthetic strategies to urethanes based on amines and CO2. Finally, the regulatory strategies on functionalization of CO2 for N-methylation/N-formylation of amines with phenylsilane and heterogeneous catalysis N-methylation of amines with CO2 and H2 are emphasized.

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A copper-catalyzed oxidative coupling reaction of arylboronic acids, amines and carbon dioxide using molecular oxygen as the oxidant

Abstract: A Cu-catalyzed oxidative coupling reaction of arylboronic acids, amines and carbon dioxide is described, providing a route to O-aryl carbamates.

Cited by 44 publications

References 55 publications

Recent Advances in the Chemistry of Metal Carbamates

Recent Advances in the Chemistry of Metal Carbamates

Construction of C–Cu Bond: A Useful Strategy in CO₂ Conversion

Catalytic Conversion of Carbon Dioxide through C-N Bond Formation

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A copper-catalyzed oxidative coupling reaction of arylboronic acids, amines and carbon dioxide using molecular oxygen as the oxidant

Abstract: A Cu-catalyzed oxidative coupling reaction of arylboronic acids, amines and carbon dioxide is described, providing a route to O-aryl carbamates.

Cited by 44 publications

References 55 publications

Recent Advances in the Chemistry of Metal Carbamates

Recent Advances in the Chemistry of Metal Carbamates

Construction of C–Cu Bond: A Useful Strategy in CO2 Conversion

Catalytic Conversion of Carbon Dioxide through C-N Bond Formation

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Product

Resources

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Construction of C–Cu Bond: A Useful Strategy in CO₂ Conversion