Selective Aryne Formation via Grob Fragmentation from the [2+2] Cycloadducts of 3-Triflyloxyarynes

Shi, Jiarong; Xu, Hai; Qiu, Dong; He, Jibo; Li, Yang

doi:10.1021/jacs.6b12161

Cited by 68 publications

(23 citation statements)

References 57 publications

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“…A single intriguing example of aryne formation with subsequent capture with a sulfoxide was reported by the same group shortly thereafter (Scheme 48c). 171 Employing 3-triflyloxyarynes in [2 + 2]-cycloadditions, the authors were able to form benzocyclobutanes 294 , which were readily opened via Grob fragmentation to afford new arynes. Apart from several other nucleophiles, the reaction with a sulfoxide was also reported, affording 296 as a single regioisomer.…”

Section: Sulfoxidesmentioning

confidence: 99%

Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts

et al. 2019

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Organosulfur compounds have long played a vital role in organic chemistry and in the development of novel chemical structures and architectures. Prominent among these organosulfur compounds are those involving a sulfur(IV) center, which have been the subject of countless investigations over more than a hundred years. In addition to a long list of textbook sulfur-based reactions, there has been a sustained interest in the chemistry of organosulfur(IV) compounds in recent years. Of particular interest within organosulfur chemistry is the ease with which the synthetic chemist can effect a wide range of transformations through either bond formation or bond cleavage at sulfur. This review aims to cover the developments of the past decade in the chemistry of organic sulfur(IV) molecules and provide insight into both the wide range of reactions which critically rely on this versatile element and the diverse scaffolds that can thereby be synthesized.

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Section: Sulfoxidesmentioning

confidence: 99%

Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts

et al. 2019

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“…Along with our study on aryne chemistry and in line with our goal of preparing biologically active as well as medicinally important molecules using these procedures,– we envisioned that switching the 2,3‐aryne ii reaction partner from an ene–arynophile to one that could incorporate two substituents other than hydrogen would enable aryne trifunctionalization. 1,3‐Dienes were thus chosen, and 1,2,3‐trisubstituted arenes with [6, n ,6]‐tricyclic system could be conceived through a cascade nucleophilic and [4+2] cycloaddition process with our domino aryne precursors (Scheme b).…”

Section: Methodsmentioning

confidence: 99%

Arene Trifunctionalization with Highly Fused Ring Systems through a Domino Aryne Nucleophilic and Diels–Alder Cascade

Jia

Tan

et al. 2019

Angewandte Chemie

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Scheme 1. Backgrounda nd proposal. Nu = nucleophile, Tf = trifluoromethanesulfonyl, TMS = trimethylsilyl.Scheme 3. Substrate scope. [a] Conditions A: slow addition of asolution of 1a (0.6 mmol) in PhCl (10 mL) to asuspension of 5 (0.3 mmol), Cs 2 CO 3 (1.8 mmol), and 18-crown-6 (0.6 mmol) in PhCl (20 mL) at 130 8 8Cover 1h.[b] Yields of isolated products. [c] Conditions B: slow addition of asolution of 1k (0.6 mmol) in toluene (10 mL) to asuspension of 5 (0.3 mmol), Cs 2 CO 3 (1.8 mmol), and 18-crown-6 (0.6 mmol) in toluene (20 mL) at 100 8 8Cover 1h.[ d] 38 %of6n with (1.5:1 d.r.) was obtained using conditions A. Angewandte Chemie Communications

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“…An aryne generation ( Scheme 13 ) was also used for the synthesis of a key intermediate of the potent antitumor PARP inhibitor – niraparib – containing an indazole core [ 113 ]. A substituted 2,3-aryne was generated in situ from (siloxy)benzocyclobutenes and CsF but the regioselectivity was poor: a ratio of both possible regioisomers of 45:55 was obtained.…”

Section: Reviewmentioning

confidence: 99%

[3 + 2]-Cycloaddition reaction of sydnones with alkynes

Hladíková¹,

Váňa²,

Hanusek³

2018

Beilstein J. Org. Chem.

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This review covers all known examples of [3 + 2]-cycloaddition between sydnones and both terminal as well as internal alkynes/cycloalkynes taken from literature since its discovery by Huisgen in 1962 up to the current date. Except enumeration of synthetic applications it also covers mechanistic studies, catalysis, effects of substituents and reaction conditions influencing reaction rate and regioselectivity.

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Selective Aryne Formation via Grob Fragmentation from the [2+2] Cycloadducts of 3-Triflyloxyarynes

Cited by 68 publications

References 57 publications

Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts

Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts

Arene Trifunctionalization with Highly Fused Ring Systems through a Domino Aryne Nucleophilic and Diels–Alder Cascade

[3 + 2]-Cycloaddition reaction of sydnones with alkynes

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