A copper-based catalytic system for carboxylation of terminal alkynes: synthesis of alkyl 2-alkynoates

Inamoto, Kiyofumi; Asano, Narumi; Kobayashi, Koji; Yonemoto, Misato; Kondo, Yoshinori

doi:10.1039/c2ob06884b

Cited by 97 publications

(44 citation statements)

References 27 publications

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“…as the base and alkyl bromides or iodides as alkylating agents. [154] However, the IMes·HCl and IPr·HCl ligands did not provide good product yields (24 and 20 %). Interestingly, Yu and Zhang reported the carboxylation of terminal alkynes with CO 2 by Cu(NHC) complexes in the presence of CuCl, Cs 2 CO 3 , and a series of NHC ligands through CÀH bond activation at ambient conditions (RT, 1 bar CO 2 ) in DMF [Eq.…”

Section: Cu-catalyzed Transformations By Using Silicon Compounds and mentioning

confidence: 98%

Recent Advances in Carbon Dioxide Capture, Fixation, and Activation by using N‐Heterocyclic Carbenes

2014

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In the last two decades, CO2 emission has caused a lot of environmental problems. To mitigate the concentration of CO2 in the atmosphere, various strategies have been implemented, one of which is the use of N-heterocyclic carbenes (NHCs) and related complexes to accomplish the capture, fixation, and activation of CO2 effectively. In this review, we summarize CO2 capture, fixation, and activation by utilizing NHCs and related complexes; homogeneous reactions and their reaction mechanisms are discussed. Free NHCs and NHC salts can capture CO2 in both direct and indirect ways to form imidazolium carboxylates, and they can also catalyze the reaction of aromatic aldehydes with CO2 to form carboxylic acids and derivatives. Moreover, associated with transition metals (TMs), NHCs can form NHC-TM complexes to transform CO2 into industrial acid or esters. Non-metal-NHC complexes can also catalyze the reactions of silicon and boron complexes with CO2 . In addition, catalytic cycloaddition of epoxides with CO2 is another effective function of NHC complexes, and NHC ionic liquids perform excellently in this aspect.

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Section: Cu-catalyzed Transformations By Using Silicon Compounds and mentioning

confidence: 98%

Recent Advances in Carbon Dioxide Capture, Fixation, and Activation by using N‐Heterocyclic Carbenes

2014

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“…These observations suggest that strong coordination between the electron-rich metal center and ligand activates the CO 2 Terminal alkynes display relatively acidic C-H bonds (pK a * 25) and can undergo carboxylation at elevated temperatures and pressures [40,41]. In the presence of a catalyst [58], mild carboxylations have been reported with copper and silver salts, both with [59][60][61] and without [62][63][64][65] external halide reagents to trap the formed carboxylate ( Fig. 6).…”

Section: Catalytic Carboxylation Of Organometallic Reagentsmentioning

confidence: 93%

Making C–C Bonds from Carbon Dioxide via Transition-Metal Catalysis

Yeung

Dong

2014

Top Catal

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“…In 2012, Kondo and co-workers reported another protocol for the carboxylative alkylation of terminal alkynes [92]. Using 8 mol% of CuI as precatalyst, 80 C was needed for the coupling of phenylacetylene, CO 2 (1 atm), and 1 equiv.…”

Section: Copper-catalyzed Reactionsmentioning

confidence: 99%

Transition Metal-Catalyzed Carboxylation of Organic Substrates with Carbon Dioxide

Brill

Lazreg

Cazin

et al. 2015

Topics in Organometallic Chemistry

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The development of sustainable chemical processes is a long-standing challenge. Carbon dioxide represents a renewable C1 building block for organic synthesis and industrial applications as an alternative to other common feedstocks which are based on natural gas, petroleum oil, or coal. Apart from the advantages associated with the nontoxicity and abundance of CO 2 , its utilization further enables the reduction in its atmospheric content, which contributes significantly to the greenhouse effect. Although widespread application of CO 2 in organic synthesis -even on an industrial scale -will not be able to fully compensate for the steadily increasing atmospheric quantities produced (mainly by the combustion of fuels), ecological and economical factors make its usage highly desirable. Therefore, tremendous efforts toward activation and utilization of CO 2 have been made by the scientific community over the last 30 years, and, as a result, the number of highly efficient transition metal-catalyzed CO 2 -incorporative reactions has increased dramatically, especially within the last decade. The achievements in the development of sustainable and economic chemical processes for the carboxylation of organic molecules with CO 2 are presented in detail in this chapter.

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A copper-based catalytic system for carboxylation of terminal alkynes: synthesis of alkyl 2-alkynoates

Abstract: An efficient coupling of terminal alkynes and CO(2) in the presence of alkyl halides can be achieved under ambient conditions using a copper/phosphine catalyst system, providing facile access to a variety of functionalised alkyl 2-alkynoates.

Cited by 97 publications

References 27 publications

Recent Advances in Carbon Dioxide Capture, Fixation, and Activation by using N‐Heterocyclic Carbenes

Recent Advances in Carbon Dioxide Capture, Fixation, and Activation by using N‐Heterocyclic Carbenes

Making C–C Bonds from Carbon Dioxide via Transition-Metal Catalysis

Transition Metal-Catalyzed Carboxylation of Organic Substrates with Carbon Dioxide

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