Iron-catalyzed oxidative cyclization of olefinic 1,3-dicarbonyls with ketone C(sp<sup>3</sup>)–H bonds: facile access to 2,3-dihydrofurans

Kang, Qing‐Qing; Meng, Yanan; Zhang, Jun-Hao; Li, Long; Ge, Guo‐Ping; Zheng, Hang; Liu, Hongxin; Wei, Wanzhi

doi:10.1039/d1nj02378k

Cited by 7 publications

(3 citation statements)

References 71 publications

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“…Based on these aforementioned results and the previous reports, 5,[10][11][12] a possible mechanism is outlined using N-methacryloyl-2-arylbenzoimidazoles 1a as a representative substrate (Scheme 3). Initially, acetonitrile or acetone undergoes thermal homolysis to form α-nitrile or α-ketone carbon radical under catalytic oxidation system.…”

Section: Scheme 2 Control Experimentsmentioning

confidence: 60%

Radical Cyclization of N-Methacryloyl-2-arylbenzoimidazoles with Nitriles, Ketones, and tert-Butyl Nitrite under Mild Conditions

et al. 2022

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We describe a method for radical cyclization of N-methacryloyl-2-arylbenzoimidazoles with nitriles, ketones, and tert-butyl nitrite (TBN) for the preparation of benzimidazo[2,1-a]isoquinolin-6(5H)-ones with the advantage of mild reaction conditions, excellent functional group compatibility and broad substrate scope. The present strategy has favorable characteristics: (1) the use of cheap metal catalysis; (2) N-radical initiated cyclization of N-methacryloyl-2-arylbenzoimidazoles; (3) rare example of radical C(sp3)–H functionalization in this cyclization.

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Section: Scheme 2 Control Experimentsmentioning

confidence: 60%

Radical Cyclization of N-Methacryloyl-2-arylbenzoimidazoles with Nitriles, Ketones, and tert-Butyl Nitrite under Mild Conditions

et al. 2022

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“…55 Our group reported the Fe-catalyzed oxidative cyclization of olefinic dicarbonyl compounds with ketone as another radical source through C–C and C–O bond formations in 2021. 56 The synthetic application of this process was illustrated by the gram-scale preparation of 97a . Importantly, α,α-dibromoketone 99 could be synthesized through a ring-opening process of 97a with N -bromosuccinimide (NBS) in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO).…”

Section: Intermolecular Cyclization Initiated By Directed C(sp3)–h Ox...mentioning

confidence: 99%

C-centered radical-initiated cyclization by directed C(sp³)–H oxidative functionalization

Mei

et al. 2022

Org. Chem. Front.

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“…Following Fe-catalyzed oxidation, the resulting oxonium cation can be deprotonated to afford the final dihydrofuran. Further, this inter-/intramolecular radical addition/cyclization methodology has been applied for the synthesis of various substituted dihydropyrans [ 100 – 101 ] and dihydrofurans [ 102 ].…”

Section: Reviewmentioning

confidence: 99%

Iron-catalyzed domino coupling reactions of π-systems

Pounder¹,

Tam²

2021

Beilstein J. Org. Chem.

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The development of environmentally benign, inexpensive, and earth-abundant metal catalysts is desirable from both an ecological and economic standpoint. Certainly, in the past couple decades, iron has become a key player in the development of sustainable coupling chemistry and has become an indispensable tool in organic synthesis. Over the last ten years, organic chemistry has witnessed substantial improvements in efficient synthesis because of domino reactions. These protocols are more atom-economic, produce less waste, and demand less time compared to a classical stepwise reaction. Although iron-catalyzed domino reactions require a mindset that differs from the more routine noble-metal, homogenous iron catalysis they bear the chance to enable coupling reactions that rival that of noble-metal-catalysis. This review provides an overview of iron-catalyzed domino coupling reactions of π-systems. The classifications and reactivity paradigms examined should assist readers and provide guidance for the design of novel domino reactions.

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Iron-catalyzed oxidative cyclization of olefinic 1,3-dicarbonyls with ketone C(sp³)–H bonds: facile access to 2,3-dihydrofurans

Abstract: Iron-catalyzed oxidative cyclization of oleﬁnic 1,3-dicarbonyls with ketone C(sp3)–H bonds through C-C and C-O bond formations has been described for the first time. A broad substrate scope and ease of...

Cited by 7 publications

References 71 publications

Radical Cyclization of N-Methacryloyl-2-arylbenzoimidazoles with Nitriles, Ketones, and tert-Butyl Nitrite under Mild Conditions

Radical Cyclization of N-Methacryloyl-2-arylbenzoimidazoles with Nitriles, Ketones, and tert-Butyl Nitrite under Mild Conditions

C-centered radical-initiated cyclization by directed C(sp³)–H oxidative functionalization

Iron-catalyzed domino coupling reactions of π-systems

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Iron-catalyzed oxidative cyclization of olefinic 1,3-dicarbonyls with ketone C(sp3)–H bonds: facile access to 2,3-dihydrofurans

Abstract: Iron-catalyzed oxidative cyclization of oleﬁnic 1,3-dicarbonyls with ketone C(sp3)–H bonds through C-C and C-O bond formations has been described for the first time. A broad substrate scope and ease of...

Cited by 7 publications

References 71 publications

Radical Cyclization of N-Methacryloyl-2-arylbenzoimidazoles with Nitriles, Ketones, and tert-Butyl Nitrite under Mild Conditions

Radical Cyclization of N-Methacryloyl-2-arylbenzoimidazoles with Nitriles, Ketones, and tert-Butyl Nitrite under Mild Conditions

C-centered radical-initiated cyclization by directed C(sp3)–H oxidative functionalization

Iron-catalyzed domino coupling reactions of π-systems

Contact Info

Product

Resources

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Iron-catalyzed oxidative cyclization of olefinic 1,3-dicarbonyls with ketone C(sp³)–H bonds: facile access to 2,3-dihydrofurans

C-centered radical-initiated cyclization by directed C(sp³)–H oxidative functionalization