Cobalt(<scp>iii</scp>)-catalyzed redox-neutral [4+2]-annulation of <i>N</i>-chlorobenzamides/acrylamides with alkylidenecyclopropanes at room temperature

Ramesh, Balu; Jeganmohan, Masilamani

doi:10.1039/d1cc00654a

Cited by 28 publications

(16 citation statements)

References 60 publications

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“…13 C NMR (100 MHz, CDCl 3 ):  = 217. 7,165.8 (d,J = 253.1 Hz),161.7,141.0 (d,J = 10.1 Hz),140.0,134.7,130.6 (d,J = 10.2 Hz),130.4 (d,J = 5.7 Hz),129.3 (d,J = 12.9 Hz),128.3,122.3 (d,J = 1.7 Hz),115.0 (d,J = 23.7 Hz),114.4 (d,J = 3.5 Hz),110.0 (d,J = 23.2 Hz),101.6,56.0,38.3,36.4,31.2,15.8…”

Section: -Fluoro-3a-hydroxy-11a-methyl-10-phenyl-33a1111a-tetrahydro-...mentioning

confidence: 99%

“…Intriguingly, we have noticed the activity of N -chlorobenzamides in the field of C–H activation for the role of internal oxidant, and the N–Cl bond may increase reactivity under mild reaction. 6 Recently, Jeganmohan’s group developed a redox-neutral [4+2] annulation of N -chlorobenzamides/acrylamides with alkylidenecyclopropanes at room temperature 7 (Scheme 1b ). The high oxidation reactivity of N -chlorobenzamides is derived from the presence of N–Cl bond to promote a mild reaction pathway at room temperature.…”

Section: Table 1 Optimization Of the Reaction Condition...mentioning

confidence: 99%

“…[4+2] annulation of Nchlorobenzamides/acrylamides with alkylidenecyclopropanes at room temperature 7 (Scheme 1b). The high oxidation reactivity…”

mentioning

confidence: 99%

“…H NMR (400 MHz, Chloroform-d) δ 8.27(d, J = 8.6 Hz, 1H), 7.54 (dd, J = 8.6, 1.9 Hz, 1H),7.52 -7.40 (m, 3H), 7.37 (d, J = 1.9 Hz, 1H),7.25 -7.18 (m, 2H), 5.57 (brs, 1H), 3.48 (ddd, J = 13.9, 9.2, 3.5 Hz, 1H), 3.08(d, J = 17.5 Hz, 1H), 2.80(d, J = 17.5 Hz, 1H), 2.67 -2.59 (m, 1H), 2.53 -2.43 (m, 1H), 2.32 -2.20 (m, 1H), 1.24 (s, 3H).13 C NMR (100 MHz, Chloroform-d) δ 217 7,. 161.9, 140.1, 139.8, 134.5, 130.4, 130.4, 129.6, 129.4, 129.2, 129.2, 128.5, 128.4, 127.3, 124.3, 113.9, 101.6, 56.0, 38.3, 36.4, 30.9, 15.8.…”

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confidence: 99%

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Cobalt(III)-Catalyzed C–H Activation/Annulation Cascade Reaction of N-Chlorobenzamides with 2-Acetylenic Ketones at Room Temperature

Zheng

et al. 2022

Synthesis

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A mild cascade annulation of Co(III)-catalyzed N-chlorobenzamide with 2-acetylenic ketones at room temperature has been reported. This reaction sets N-Cl bond of N-chlorobenzamide as an internal oxidant, displaying broad functional group tolerance and excellent reverse selectivity of alkyne insertion under mild and safe conditions. The cascade reaction offers a straightforward and mild protocol to construct isoquinolones with high yields at room temperature.

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Section: -Fluoro-3a-hydroxy-11a-methyl-10-phenyl-33a1111a-tetrahydro-...mentioning

confidence: 99%

Section: Table 1 Optimization Of the Reaction Condition...mentioning

confidence: 99%

“…[4+2] annulation of Nchlorobenzamides/acrylamides with alkylidenecyclopropanes at room temperature 7 (Scheme 1b). The high oxidation reactivity…”

mentioning

confidence: 99%

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confidence: 99%

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Cobalt(III)-Catalyzed C–H Activation/Annulation Cascade Reaction of N-Chlorobenzamides with 2-Acetylenic Ketones at Room Temperature

Zheng

et al. 2022

Synthesis

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“…Synthesis of 6. 20 To a solution of 3a (45 mg, 0.17 mmol) in THF (4 mL) was added LiAlH 4 (0.56 mL, 1 M in THF). The resulting mixture was heated at reflux (oil bath) for 8 h under an argon atmosphere.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Synthesis of Dihydroquinolinone Derivatives via the Cascade Reaction of o-Silylaryl Triflates with Pyrazolidinones

Shen

Zhao

et al. 2021

J. Org. Chem.

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Presented herein is a novel synthesis of dihydroquinolinone derivatives through an unprecedented cascade reaction of o-silylaryl triflates with pyrazolidinones. Mechanistically, the formation of the title products is believed to involve a cascade procedure including in situ formation of aryne and its addition with pyrazolidinone followed by N−N bond cleavage and intramolecular C−C bond formation/annulation. Compared with literature methods for the synthesis of dihydroquinolinones, this protocol has advantages such as multistep transformations accomplished in one pot, broad substrate scope, mild reaction conditions, and good tolerance of diverse functional groups. In addition, the products thus obtained demonstrated significant in vitro antiproliferative activity in selected human cancer cell lines.

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Cp*Co(III)‐Catalyzed CH Functionalization Mediated by Oxidizing Directing Groups toward the Synthesis of Heterocycles

Aher¹,

Mondal²,

Pawar³

2022

Handbook of CH-Functionalization

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The utilization of oxidizing directing group for CH activation/functionalization is a unique strategy for the synthesis of a versatile range of heterocycles under redox‐neutral conditions. In this approach, the directing group plays a dual role; controls the product selectivity through its chelation property, and a part of the directing group functions as an internal oxidant. The oxidizing property of the directing groups is due to the oxidizing ability of the NO, NN, NS, NCl bonds. Overall, this synthetic strategy precludes the need for external oxidants, thereby making the process environmentally benign. This article describes significant developments in this area focusing on the Cp*Co(III)‐catalyzed CH functionalization using the oxidizing directing group strategy for the synthesis of heterocycles. The emphasis has been given to the scope and generality of the reactions along with their mechanistic understanding.

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Cobalt(iii)-catalyzed redox-neutral [4+2]-annulation of N-chlorobenzamides/acrylamides with alkylidenecyclopropanes at room temperature

Abstract: An efficient synthesis of substituted 3,4-dihydroisoquinolinones through [4+2]-annulation of N-chlorobenzamides/acrylamides having a monodentate directing group with alkylidenecyclopropanes in the presence of a less expensive, highly abundant and air stable Co(III)...

Cited by 28 publications

References 60 publications

Cobalt(III)-Catalyzed C–H Activation/Annulation Cascade Reaction of N-Chlorobenzamides with 2-Acetylenic Ketones at Room Temperature

Cobalt(III)-Catalyzed C–H Activation/Annulation Cascade Reaction of N-Chlorobenzamides with 2-Acetylenic Ketones at Room Temperature

Synthesis of Dihydroquinolinone Derivatives via the Cascade Reaction of o-Silylaryl Triflates with Pyrazolidinones

Cp*Co(III)‐Catalyzed CH Functionalization Mediated by Oxidizing Directing Groups toward the Synthesis of Heterocycles

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