Trifluoromethanesulfonic Acid Catalyzed Synergetic Oxidative/[3+2] Cyclization of Quinones with Olefins

Meng, Lingkui; Zhang, Guanghui; Liu, Chao; Wu, Kun; Lei, Aiwen

doi:10.1002/anie.201305885

Cited by 33 publications

(9 citation statements)

References 58 publications

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“…Afterwards, at rifluoromethanesulfonic acid (HOTf)-catalyzed synergetic oxidative/[3+ +2] cyclization of quinones with olefins was demonstrated by the same group. [23] Notably,b oth symmetric and asymmetric tetrahydrobenzodifurans could be synthesized in good yields with variousk inds of olefins (Scheme 11). Notably,t he tetrahydrobenzodifurans obtained could be easily transformed into the corresponding benzodifuransi na lmost quantitative yield with DDQ as the oxidant Scheme8.Selectivities of alkyl radical addition to BQs.…”

Section: Alkyl Radical Additionmentioning

confidence: 99%

Carbon‐Centered Radical Addition to C=X Bonds for C−X Bond Formation

Liu

Lei

2015

Chemistry An Asian Journal

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Among various kinds of radical reactions, the addition of carbon-centered radicals to unsaturated bonds represents a powerful tool for the construction of different C-C and C-X (X = N, O, S, etc.) bonds, in which typically applied unsaturated bonds include alkenes, alkynes, imines, carbonyls, and even thiocarbonyls. When C=X bonds are utilized as the radical acceptors, reactions usually occur at the carbon position to generate a heteroatom radical, during which C-C coupling products are formed. This reaction mode has dominated this field for several decades. However, there is also another unconventional type of radical addition mode, in which carbon-centered radicals attack the heteroatom position of C=X bonds to generate carbon radicals, during which selective C-X bond formation is achieved. This reaction mode demonstrates an effective method for the construction of different C-X bonds, such as C-O, C-N, and C-S bonds. This Focus Review gives an overview of recent advances in this unconventional field.

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Section: Alkyl Radical Additionmentioning

confidence: 99%

Carbon‐Centered Radical Addition to C=X Bonds for C−X Bond Formation

Liu

Lei

2015

Chemistry An Asian Journal

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“…54 [3+2] Cycloaddition of quinones has proved successful also for the synthesis of structurally more complex DHB skeletons. Examples are the synthesis of tetrahydrobenzodifurans by HOTf-catalyzed direct oxidative C-H functionalization of p-benzoquinone with alkenes from 2013 by Lei and co-workers, 55…”

Section: Review Syn Thesismentioning

confidence: 99%

Recent Advances in Synthetic Strategies to 2,3-Dihydrobenzofurans

Laurita

D’Orsi²,

Chiummiento³

et al. 2020

Synthesis

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This review gives an overview on recent developments in methods for the construction of compounds with the 2,3-dihydrobenzofuran core in the period 2012 to 2019. Interest in 2,3-dihydrobenzofurans is constantly increasing. The methods are divided into intermolecular and intramolecular approaches. Intermolecular approaches are subdivided according to the parent intermediate for the key reaction, while intermolecular approaches are subdivided according by which bond is formed in the key reaction. The transformation of benzofurans to dihydrobenzofurans and other miscellaneous methods are also discussed. Approaches useful for the synthesis of natural products are emphasized.1 Introduction2 Intermolecular Approaches2.1 o-Quinone Methides and o-Quinones2.2 p-Quinone Methides and p-Quinones2.3 Nitrogen-Containing Phenols and Quinones2.4 o-Hydroxyphenylcarbonyl Derivatives and Phenols2.5 Miscellaneous3 Intramolecular Approaches3.1 O–C2 Bond Forming3.2 C2–C3 Bond Forming3.3 C3–Aryl Bond Forming3.4 O–Aryl Bond Forming4 From BF to DHB5 Rearrangements and Aromatizations

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“…The failure to trap radical intermediate with TEMPO was not sufficient to prove a non-radical addition process, because of the possibility that the oxidative cyclization took place immediately after the phenoxyl radical had been generated. 15 Equation 3 Control experiment by addition of TEMPO Therefore, a possible mechanism for this reaction is presented in Scheme 4. When heated, S 2 O 8 2obtains an electron from 1a and is reduced to SO 4…”

Section: Equation 2 One-step Synthesis Of Corsifuran Amentioning

confidence: 99%