Enantioselective Cross‐couplings between Halide Derivatives and Organometallics by Using Iron and Cobalt Catalysts: Formation of C−C Bonds

Shu, Tao; Cossy, Janine

doi:10.1002/chem.202101363

Cited by 19 publications

(1 citation statement)

References 29 publications

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“…By increasing the loading of cobalt catalysts, the ratio of uncyclized 13 to cyclized 14 products did increase. This linear relationship suggested that the cyclization step did not involve metal, which supports a radical mechanism . These control experiments indicated that the reaction should undergo a radical pathway.…”

Section: Resultsmentioning

confidence: 68%

Cobalt-Catalyzed Enantioconvergent Negishi Cross-Coupling of α-Bromoketones

Wang,

Shen,

Chen

et al. 2023

J. Am. Chem. Soc.

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Cobalt-catalyzed enantioconvergent cross-coupling of α-bromoketones with aryl zinc reagents is achieved to access chiral ketones bearing α-tertiary stereogenic centers with high enantioselectivities. The more challenging and sterically hindered α-bromoketones bearing a 2-fluorophenyl group or β-secondary and tertiary alkyl chains could also be well-tolerated. Adjusting the electronic effect of chiral unsymmetric N,N,N-tridentate ligands is critical for improving the reactivity and selectivity of this transformation, which is beneficial for further studies of asymmetric 3d metal catalysis via ligand modification. The control experiments and kinetic studies illustrated that the reaction involved radical intermediates and the reductive elimination was a rate-determining step.

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Section: Resultsmentioning

confidence: 68%

Cobalt-Catalyzed Enantioconvergent Negishi Cross-Coupling of α-Bromoketones

Wang,

Shen,

Chen

et al. 2023

J. Am. Chem. Soc.

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Iron‐Catalyzed Enantioselective CH Functionalization

Asako

Ilies

2022

Handbook of CH-Functionalization

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Because of the combined attractive features of iron as a sustainable catalyst and of CH functionalization, over the past several decades the chemistry of iron‐catalyzed CH functionalization has attracted much attention and is growing rapidly. This article briefly introduces the recent emergence of iron‐catalyzed enantioselective CH functionalization reactions that have been achieved by controlling the reactivity and coordination environment of active iron species by chiral ligands.

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An Efficient Route to 3,3′‐Biindolinylidene‐diones by Iron‐Catalyzed Dimerization of Isatins

Jagtap

Pradhan

Gonnade

et al. 2022

Chemistry An Asian Journal

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Iron-catalyzed dimerization of various isatin derivatives is described for the efficient synthesis of 3,3'-biindolinylidene-diones (isoindigos). The reaction provides easy access to self-coupled and cross-coupled 3,3'-indolinylidene-diones that have high relevance to biology and materials. This Fe(0)or Fe(II)-catalyzed dimerization reaction tolerates a wide range of functionalities, such as fluoro, chloro, bromo, alkenyl, nitrile, ether, ester, pyrrolyl, indolyl and carbazolyl groups, including cyclic and acyclic alkyls as well as an alkyl-bearing fatty-alcohol moiety. Especially, the coupling between two distinct isatins provided excellent selectivity for the crossdimerization with trace of self-couplings. The single-crystal Xray diffraction study established the molecular structure of eight dimerized products. A preliminary mechanistic study of the Fe-catalyzed dimerization supported the radical pathway for the reaction.

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Enantioselective Cross‐couplings between Halide Derivatives and Organometallics by Using Iron and Cobalt Catalysts: Formation of C−C Bonds

Cited by 19 publications

References 29 publications

Cobalt-Catalyzed Enantioconvergent Negishi Cross-Coupling of α-Bromoketones

Cobalt-Catalyzed Enantioconvergent Negishi Cross-Coupling of α-Bromoketones

Iron‐Catalyzed Enantioselective CH Functionalization

An Efficient Route to 3,3′‐Biindolinylidene‐diones by Iron‐Catalyzed Dimerization of Isatins

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