Visible-Light Photoredox Catalyzed Double C–H Functionalization: Radical Cascade Cyclization of Ethers with Benzimidazole-Based Cyanamides

Jiang, Si; Tian, Xiumei; Feng, Shuyao; Li, Jiang-Sheng; Li, Zhiwei; Lu, Chunmei; Li, Chao‐Jun; Liu, Weidong

doi:10.1021/acs.orglett.0c03853

Cited by 33 publications

(12 citation statements)

References 45 publications

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“…11 In particular, in view of the widespread existence and significant prominence of ether moieties in various agrochemicals and pharmaceuticals, CDC reactions using ethers as coupling partners have spurred a speedy development over the past few years. 12 On the other hand, with the increasing demand of green chemistry and energy conservation, significant efforts have been made toward visible-light-induced CDC reactions promoted by transition-metal based photocatalysts 13 or metal-free organic catalysts, 14 while the later became more appealing with regard to their environmental friendliness. While a plethora of breakthroughs have been established in photoinduced CDC coupling of ethers (or alkanes) with arenes and heteroarenes, 15 to the best of knowledge, the C(sp 2 )–C(sp 3 ) coupling of synthetically crucial and electron-rich and olefinic enamide scaffolds with ethers or even alkanes via photoinitiated transformations appears to be underdeveloped.…”

Section: Introductionmentioning

confidence: 99%

Transition-metal-free regioselective and stereoselective C(sp²)–C(sp³) coupling of enamides with ethers or alkanes via photoredox-catalyzed cross-dehydrogenative coupling reactions

et al. 2022

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Section: Introductionmentioning

confidence: 99%

Transition-metal-free regioselective and stereoselective C(sp²)–C(sp³) coupling of enamides with ethers or alkanes via photoredox-catalyzed cross-dehydrogenative coupling reactions

et al. 2022

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“…[ 34 ] Using visible light, a C sp 3‐C sp 2 CDC reaction occurred between ether and arene with an insertion of nitrile in between (Scheme 3h). [ 35 ]…”

Section: Cdc Of α‐C—h Bond To Oxygenmentioning

confidence: 99%

On Inventing Cross‐Dehydrogenative Coupling (CDC): Forming C—C Bond from Two Different C—H Bonds

2022

Chin. J. Chem.

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Comprehensive Summary Constructing C—C bonds is central to the synthesis of all chemical products. While conventional C—C bond formation methods always require one or two functional groups, 20 years ago, our establishment of the concept of Cross‐Dehydrogenative Coupling (CDC), wherein C—C bonds are directly formed from two different C—H bonds via the “formal” removal of two H atoms, has revolutionized chemical synthesis and has become one of the most active research subjects in chemistry. This perspective article will provide an insight of the origin of this concept and its early development in our laboratory. What are your favorite scientific discoveries from your lab? Over the past 30 years, we have made many discoveries. The most important ones are the developments of various Grignard‐type reactions in water which contradict textbook knowledge, the Aldehyde‐Alkyne‐Amine (A3) coupling, the Cross‐Dehydrogenative Coupling that forms C—C bond from two C—H bonds, and the umpolung of carbonyl as organometallic reagent surrogate that allows to carry out organometallic reactions without using stoichiometric organometallic reagents. Did you plan to be a chemist when you were young? Not really. I was planning to be an artist when I was young but really felt deep affection for chemistry after I entered college. How did you get into Green Chemistry? When I was a graduate student, I became fascinated about natural product synthesis. However, I felt that most reported total syntheses are very lengthy and difficult. As a result, I have been constantly asking myself: can we have novel chemistry to simplify organic syntheses? By coincidence, this was also during the dawn of Green Chemistry, which has the same philosophy. Besides chemistry, what are your hobbies? Besides chemistry research, I still have an eye on art. Also, I enjoy reading philosophy books, traveling and meeting people from different walks of life. What advice do you give to young academics? Be unique, creative and different from others. These might be difficult to do at the beginning but they will be beneficial in the long run. In your personal view, what are the important future developments for chemistry? As chemistry is the central science, important future developments will mostly arise from interdisciplinary areas. These are already occurring between biology and chemistry, environment and chemistry, materials and chemistry, energy and chemistry, but will also be between chemistry and some emerging fields. One of them is with artificial intelligence. Currently, it requires a great amount of time and effort to carry out a large number of experiments for most reactions, Artificial intelligence can greatly change and simplify future chemistry research.

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“…137,138 The first example of the visible-light photoredox-catalyzed cyclization of N-cyanobenzimidazoles was proposed by Li and coworkers in 2021 (Scheme 71). 140 This method realized sequential inert C(sp 3 )-H/C(sp 2 )-H functionalization under mild conditions, representing a simple and sustainable approach to valuable tetracyclic benzo [4,5]imidazo[1,2-c]quinazolines. The radical inhibition experiment using TEMPO, BHT, and DPE suggested that the tetrahydrofuran radical is an important intermediate.…”

Section: Radical Cyclization With Other Substratesmentioning

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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Visible-Light Photoredox Catalyzed Double C–H Functionalization: Radical Cascade Cyclization of Ethers with Benzimidazole-Based Cyanamides

Cited by 33 publications

References 45 publications

Transition-metal-free regioselective and stereoselective C(sp²)–C(sp³) coupling of enamides with ethers or alkanes via photoredox-catalyzed cross-dehydrogenative coupling reactions

Transition-metal-free regioselective and stereoselective C(sp²)–C(sp³) coupling of enamides with ethers or alkanes via photoredox-catalyzed cross-dehydrogenative coupling reactions

On Inventing Cross‐Dehydrogenative Coupling (CDC): Forming C—C Bond from Two Different C—H Bonds

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

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Visible-Light Photoredox Catalyzed Double C–H Functionalization: Radical Cascade Cyclization of Ethers with Benzimidazole-Based Cyanamides

Cited by 33 publications

References 45 publications

Transition-metal-free regioselective and stereoselective C(sp2)–C(sp3) coupling of enamides with ethers or alkanes via photoredox-catalyzed cross-dehydrogenative coupling reactions

Transition-metal-free regioselective and stereoselective C(sp2)–C(sp3) coupling of enamides with ethers or alkanes via photoredox-catalyzed cross-dehydrogenative coupling reactions

On Inventing Cross‐Dehydrogenative Coupling (CDC): Forming C—C Bond from Two Different C—H Bonds

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

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Transition-metal-free regioselective and stereoselective C(sp²)–C(sp³) coupling of enamides with ethers or alkanes via photoredox-catalyzed cross-dehydrogenative coupling reactions

Transition-metal-free regioselective and stereoselective C(sp²)–C(sp³) coupling of enamides with ethers or alkanes via photoredox-catalyzed cross-dehydrogenative coupling reactions

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