First Cp*Co(III)-catalyzed Mizoroki-Heck coupling reactions of alkenes and aryl bromide/iodide

Srivastava, A. K.; Satrawala, Naveen; Ali, Munsaf; Sharma, Charu; Joshi, Rashika

doi:10.1016/j.tetlet.2019.151283

Cited by 11 publications

(6 citation statements)

References 45 publications

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“…Different types of cobalt species, normally generated by the combination of cobalt salts and Grignard reagents, have been shown to be effective catalysts in aryl halide cross‐coupling reactions. However, the involvement of Cp*Co intermediates in these types of transformations remains practically unexplored . Guided by our previous studies on Cp*Co III ‐catalyzed C−H functionalization, we selected an alkyne annulation as a benchmark reaction.…”

Section: Figurementioning

confidence: 99%

Weakly Coordinated Cobaltacycles: Trapping Catalytically Competent Intermediates in Cp*Co^IIICatalysis

et al. 2020

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Herein, we disclose the synthesis of metallacyclic Cp*CoIII complexes containing weakly chelating functional groups. We have employed these compounds not only as an exceptional platform for accessing some of the most widely invoked transient intermediates in C−H functionalization processes but also as competent catalysts in different Cp*Co‐catalyzed transformations, including a benchmark coupling reaction.

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Section: Figurementioning

confidence: 99%

Weakly Coordinated Cobaltacycles: Trapping Catalytically Competent Intermediates in Cp*Co^IIICatalysis

et al. 2020

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“…The first report of Mizoroki-Heck coupling of alkenes and aryl halides using Cp*Co(III) catalyst was established by Joshi et al in 2019. [57] The highly stable catalyst Cp*Co(CO)I 2 catalyzed the cross-coupling of alkenes 35 with aryl halides 1 in the presence of K 3 PO 4 and TBAB in DMF solvent (Scheme 28). The product 36 yields depended strictly on the halide type, exceptional yields were obtained with iodobenzene, bromobenzene generated low to average yields while chlorobenzenes were inactive to the reaction.…”

Section: Cobalt-catalyzed Reactionsmentioning

confidence: 99%

“…The first report of Mizoroki‐Heck coupling of alkenes and aryl halides using Cp*Co(III) catalyst was established by Joshi et al . in 2019 [57] . The highly stable catalyst Cp*Co(CO)I 2 catalyzed the cross‐coupling of alkenes 35 with aryl halides 1 in the presence of K 3 PO 4 and TBAB in DMF solvent (Scheme 28).…”

Section: Cobalt‐catalyzed Reactionsmentioning

confidence: 99%

Low‐Cost Transition Metal‐Catalyzed Heck‐Type Reactions: An Overview

2022

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Heck coupling has emerged as an effective and powerful tool for CÀ C bond formations, with applications in academic and industrial grounds. The conventional Mizoroki-Heck reaction employed expensive Pd based catalysts, however, developments to meet low-cost replacements to Pd is relevant from a sustainable point of view. Heck-type couplings involving costeffective transition metals such as Fe, Co, Ni, and Cu have been established in the recent decades. Herein, we have comprehended the developments in low-cost transition metal-catalyzed Heck couplings covering the literature from 2016.

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“…(E)-1-Methyl-4-styrylbenzene (E-1b). 20 E-1b was prepared with 4methylbenzaldehyde (2 mmol, 240 mg, 235 μL) as the substrate according to general procedure B as a white solid (217.1 mg, 56% yield, mp = 68.7−69.5 °C). (E)-1-Methyl-3-styrylbenzene (E-1c).…”

Section: ■ Conclusionmentioning

confidence: 99%

“…26 (E)-1-Chloro-4-styrylbenzene (E-1j). 20 E-1j was prepared with 4chlorobenzaldehyde (2 mmol, 280 mg) as the substrate according to general procedure B as a white solid (129.2 mg, 30% yield, mp = 129.5− 130.1 °C). 1 H NMR (400 MHz, CDCl 3 ) δ ppm 7.53 (d, J = 8 Hz, 2H), 7.47 (d, J = 8 Hz, 2H), 7.41−7.30 (m, 5H), 7.10 (d, J = 4 Hz, 2H).…”

Section: ■ Conclusionmentioning

confidence: 99%

Energy-Transfer-Mediated Photocatalysis by a Bioinspired Organic Perylenephotosensitizer HiBRCP

Zhang

Xia

et al. 2021

J. Org. Chem.

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Energy transfer plays a special role in photocatalysis by utilizing the potential energy of the excited state through indirect excitation, in which a photosensitizer determines the thermodynamic feasibility of the reaction. Bioinspired by the energy-transfer ability of natural product cercosporin, here we developed a green and highly efficient organic photosensitizer HiBRCP (hexaisobutyryl reduced cercosporin) through structural modification of cercosporin. After structural manipulation, its triplet energy was greatly improved, and then, it could markedly promote the efficient geometrical isomerization of alkenes from the E-isomer to the Z-isomer. Moreover, it was also effective for energy-transfer-mediated organometallic catalysis, which allowed realization of the cross-coupling of aryl bromides and carboxylic acids through efficient energy transfer from HiBRCP to nickel complexes. Thus, the study on the relationship between structural manipulation and their photophysical properties provided guidance for further modification of cercosporin, which could be applied to more meaningful and challenging energy-transfer reactions.

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First Cp*Co(III)-catalyzed Mizoroki-Heck coupling reactions of alkenes and aryl bromide/iodide

Cited by 11 publications

References 45 publications

Weakly Coordinated Cobaltacycles: Trapping Catalytically Competent Intermediates in Cp*Co^IIICatalysis

Weakly Coordinated Cobaltacycles: Trapping Catalytically Competent Intermediates in Cp*Co^IIICatalysis

Low‐Cost Transition Metal‐Catalyzed Heck‐Type Reactions: An Overview

Energy-Transfer-Mediated Photocatalysis by a Bioinspired Organic Perylenephotosensitizer HiBRCP

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First Cp*Co(III)-catalyzed Mizoroki-Heck coupling reactions of alkenes and aryl bromide/iodide

Cited by 11 publications

References 45 publications

Weakly Coordinated Cobaltacycles: Trapping Catalytically Competent Intermediates in Cp*CoIIICatalysis

Weakly Coordinated Cobaltacycles: Trapping Catalytically Competent Intermediates in Cp*CoIIICatalysis

Low‐Cost Transition Metal‐Catalyzed Heck‐Type Reactions: An Overview

Energy-Transfer-Mediated Photocatalysis by a Bioinspired Organic Perylenephotosensitizer HiBRCP

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Product

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Weakly Coordinated Cobaltacycles: Trapping Catalytically Competent Intermediates in Cp*Co^IIICatalysis

Weakly Coordinated Cobaltacycles: Trapping Catalytically Competent Intermediates in Cp*Co^IIICatalysis