Generation of benzosultams via trifluoromethylation of 2-ethynylbenzenesulfonamide under visible light

Xiang, Yuanchao; Kuang, Yunyan; Wu, Jie

doi:10.1039/c6qo00120c

Cited by 31 publications

(10 citation statements)

References 108 publications

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“…According to Koike and Akita in 2015 [79], using Ir(ppy)2(dtbbpy)(PF6) as a photocatalyst and 2,6-ditertbutylpyridine as a base, internal aryl alkynes and Umemoto reagent were converted into tetra-substituted trifluoromethylated alkenes in 30%-86% yields, and 61/39 to 97/3 E/Z ratios. Similar strategies were conducted by Wu [80] and Han [81,82] to achieve intramolecular trifluoromethylation cyclization and oxidative trifluoromethylation reactions, respectively (Scheme 7).…”

Section: Cf3 Radical Reagentsmentioning

confidence: 95%

Visible light promoted difunctionalization reactions of alkynes

Ren

2019

Chinese Journal of Catalysis

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Visible light promoted difunctionalization of alkynes is reviewed. The difunctionalization reaction is achieved by different reagents. Radicals such as carbon (sp 3), carbon (sp 2), and other heteroatom (P, S, N, Se, O, and halide) radicals initiated by visible light can undergo radical addition to a carbon-carbon triple bond. Upon further transformation, the desired difunctionalized products are obtained. Some organometallic complexes can be activated by visible light; the difunctionalization of alkynes is catalyzed by these species. Other reagents like 1,3-dipole precursors could also react with alkynes to give difunctionalization products; here, the 1,3-dipole derivatives are obtained by visible light photocatalysis. So far, the strategy has been succeeded in the formation of CC bonds and C-X bonds. Several valuable chemical skeletons have been constructed under mild conditions. However, high regio-and stereoselectivities in some direct difunctionalization methodologies are yet to be achieved.

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Section: Cf3 Radical Reagentsmentioning

confidence: 95%

Visible light promoted difunctionalization reactions of alkynes

Ren

2019

Chinese Journal of Catalysis

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“…Under mild visible light-photocatalytic conditions, in 2016, Wu and Kuang et al achieved a facile synthesis of benzosultams from 2-ethynylbenzenesulfonamides and Togni’s reagent ( Scheme 15 ) [ 109 ]. Ir(ppy) 3 was demonstrated as the best choice of photocatalyst, while other commonly used catalysts, such as Ru(bpy) 3 (PF 6 ) 2 or eosin Y, were ineffective.…”

Section: Visible Light Photocatalytic Synthesis Of Benzosultamsmentioning

confidence: 99%

Recent Advances in Catalytic Synthesis of Benzosultams

Zhao

2020

Molecules

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Benzosultams represent one category of multi-heteroatom heterocyclic scaffolds, which have been frequently found in pharmaceuticals, agricultural agents, and chiral catalysts. Given the diversely significant functions of these compounds in organic and medicinal chemistry, great efforts have been made to develop novel catalytic systems for the efficient construction of benzosultam motifs over the past decades. Herein, in this review, we mainly summarize the recent advances in the field of catalytic synthesis of benzosultams from 2017 to August of 2020, with an emphasis on the scopes and mechanisms of representative reactions.

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“…201 This reaction employed Togni's reagent, which was activated by ultraviolet light to generate a trifluoromethyl radical. Via a similar strategy, the authors also synthesized benzosultams via trifluoromethylation of 2-ethynylbenzenesulfonamide under visible light 202 and fluorinated 2-oxindoles. 203…”

Section: Scheme 104 Photo-promoted Synthesis Of Trimethylarylstannanesmentioning

confidence: 99%

Recent Synthetic Applications of Catalyst-Free Photochemistry

Liu¹,

Li²

2017

Synlett

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Catalyst-free photochemistry provides numerous opportunities toward sustainable synthesis because catalyst separation can usually be avoided, which is consistent with green chemistry principles. Complementary to the well-reviewed photoredox chemistry, this review specifically summarizes the synthetic applications of photochemistry without external catalysts reported since 2000. The selected examples include both natural product synthesis and new methodology development. This review is arranged based on the type of chromophore. It is our hope that this review will inspire more synthetic chemists to embrace photochemistry into their research plans.1 Introduction2 Photochemistry of Olefins2.1 [2+2] Cycloaddition of Enones and Olefins2.2 Cycloaddition of Olefins without Carbonyl Groups2.3 Z/E Isomerization2.4 Cyclization2.5 Others3 Photochemistry of C=O3.1 The Paternò–Büchi Reaction3.2 The Yang Photoenolization3.3 The Norrish Type I Reaction3.4 The Norrish Type II Reaction3.5 Others4 Photochemistry of Nitrogen-Containing Functional Groups5 Photochemistry of Halogen-Containing Compounds6 Conclusion and Outlook

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Generation of benzosultams via trifluoromethylation of 2-ethynylbenzenesulfonamide under visible light

Cited by 31 publications

References 108 publications

Visible light promoted difunctionalization reactions of alkynes

Visible light promoted difunctionalization reactions of alkynes

Recent Advances in Catalytic Synthesis of Benzosultams

Recent Synthetic Applications of Catalyst-Free Photochemistry

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