Visible-Light-Promoted Polysubstituted Olefins Synthesis Involving Sulfur Ylides as Carbene Trapping Reagents

Ye, Cong; Cai, Bao‐Gui; Lü, Juan; Cheng, Xiao; Li, Lei; Pan, Zhongwen; Xuan, Jun

doi:10.1021/acs.joc.0c02500

Cited by 49 publications

(25 citation statements)

References 66 publications

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“…Alkenes with the same pattern of substituents can also be obtained using sulfur ylides 152 as acceptors for carbenes 2 generated photochemically from aryl diazoacetates 1 (Scheme ). In this case, the elimination of dimethyl sulfide from intermediate 153 gives desired product 154 in decent yields and excellent diastereoselectivity …”

Section: Other Photochemical Reactionsmentioning

confidence: 99%

Lightening Diazo Compounds?

Durka

Turkowska

Gryko

2021

ACS Sustainable Chem. Eng.

170

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The development of new sustainable reactions and protocols is essential to fulfill the growing demands of every branch of organic chemistry for greener synthetic methodologies. In this context, the use of visible light as the only source of energy is highly appealing. Since diazo compounds are valuable reagents in organic synthesis, their transformations realized in a sustainable manner are of interest. High reactivity and easy availability make them suitable for solar-driven transformations. Indeed, photochemical reactions of diazo compounds have recently proven a valuable alternative to transition metal catalysis. In this perspective, we highlight applications of these reagents under visible irradiation, particularly focusing on recent advancements. These include photochemical generation of carbenes and radicals which involve many relevant reactions, [2+1]-cycloadditions, X−H and C−H insertions, Wolff rearrangement, and more. Mechanistic aspects of these processes are briefly addressed to give readers a deeper understanding of rules underlying photoreactivity of diazo compounds. We conclude by emphasizing significant advancements and discussing challenges for future developments in the photochemistry of these valuable reagents.

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Section: Other Photochemical Reactionsmentioning

confidence: 99%

Lightening Diazo Compounds?

Durka

Turkowska

Gryko

2021

ACS Sustainable Chem. Eng.

170

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“…此外, 该反应不仅具有很高的收率, 而且选择性也很好, 绝大多数烯烃产物的顺/反比均超过了 1∶20. 近期, 使用硫叶立德来代替重氮化合物 89, 同样实现了三取代烯烃的高效高选择性合成 [46] .…”

Section: 通过氮叶立德中间体unclassified

Visible Light-Promoted Transformation of Diazo Compounds via the Formation of Free Carbene as Key Intermediate

Cai¹,

Xuan²

2021

Chinese Journal of Organic Chemistry

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Carbene is one of the most important synthetic intermediates in organic synthesis. In the past few decades, transition-metal catalyzed carbene transfer reactions have made remarkable development. Recently, visible light-promoted transformation of diazo compounds through the formation of free carbene as key intermediate begun to rise. The reaction only need visible light as the sole energy source which meets the concept of green chemistry. Since the pioneering works developed by the groups of Diaves and Zhou, photo-promoted transformation of diazo compounds has attracted more and more attentions. On the basis of previous work, the latest progress in this field is further improved, which mainly focuses on the recent new transformation reactions of diazo compounds under visible light irradiation and the contributions reported from Chinese research group. The future development direction, as well as challenges in this field is prospected.

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“…One example of tetrasubstituted olefin synthesis was described by using the reported method in low yield because of the formation of undesired by‐products. Recently, our group developed the coupling reaction of aryl diazoacetates with sulfur ylides under blue LEDs irradiation, leading to various valuable trisubstituted olefins in a single E configuration (Scheme 1a) [14b] . The method was also limited to the synthesis of trisubstituted alkenes, and no reaction occurred when sulfur ylide with substituents at its α ‐position.…”

Section: Methodsmentioning

confidence: 99%

All‐Carbon Tetrasubstituted Olefins Synthesis from Diazo Compounds and Iodonium Ylides under Blue LED Irradiation

Zhao

et al. 2021

Adv Synth Catal

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A route for the construction of all‐carbon tetra‐substituted olefins through visible‐light promoted coupling of diazo compounds with iodonium ylides was developed. A wide range of all‐carbon tetra‐substituted olefins was obtained in moderate to good yields. The synthetic values of the current method were further approved by the synthesis of natural isolates modified alkenes and the successful transformation of final olefins into important heterocycles.

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Visible-Light-Promoted Polysubstituted Olefins Synthesis Involving Sulfur Ylides as Carbene Trapping Reagents

Cited by 49 publications

References 66 publications

Lightening Diazo Compounds?

Lightening Diazo Compounds?

Visible Light-Promoted Transformation of Diazo Compounds via the Formation of Free Carbene as Key Intermediate

All‐Carbon Tetrasubstituted Olefins Synthesis from Diazo Compounds and Iodonium Ylides under Blue LED Irradiation

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