Fe-Catalyzed Hydroalkylation of Olefins with <i>para</i>-Quinone Methides

Shen, Ying; Qi, Jifeng; Mao, Zhenjun; Cui, Sunliang

doi:10.1021/acs.orglett.6b01173

Cited by 131 publications

(32 citation statements)

References 51 publications

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“…313 The reaction is useful for the synthesis of para -substituted 2,6-di- tert -butyl phenols via a 1,6-conjugate radical addition. A variety of substituted phenols (R 4 = Me, Ar) function as competent electrophiles, and the alkene moiety may be substituted with hydrogen, alkyl, alcohol, ketone, ester and amide functional groups.…”

Section: C-c Bondsmentioning

confidence: 99%

Mn-, Fe-, and Co-Catalyzed Radical Hydrofunctionalizations of Olefins

et al. 2016

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Cofactor-mimetic aerobic oxidation has conceptually merged with catalysis of syngas reactions to form a wide range of Markovnikov-selective olefin radical hydrofunctionalizations. We cover the development of the field and review contributions to reaction invention, mechanism and application to complex molecule synthesis. We also provide a mechanistic framework for understanding this compendium of radical reactions.

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Section: C-c Bondsmentioning

confidence: 99%

Mn-, Fe-, and Co-Catalyzed Radical Hydrofunctionalizations of Olefins

et al. 2016

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“…In order to improve the synthetic potential of this methodology, the de‐ tert ‐butylation reaction was carried out according to the previous reports . At the beginning, the protection of the α ‐hydroxy group of 3 b with acetyl substituent produced the corresponding compound 4 .…”

Section: Figurementioning

confidence: 99%

Asymmetric 1,6‐Conjugate Addition of para‐Quinone Methides for the Synthesis of Chiral β,β‐Diaryl‐α‐Hydroxy Ketones

2017

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A direct asymmetric 1,6-conjugated addition of a-hydroxy ketone to para-quinone methides has been developed. It is an efficient approach to the synthesis of chiral b,b-diaryl-a-hydroxy ketones. The reaction runs smoothly in the presence of ZnEt 2 and nonracemic bis(diarylhydroxymethylpyrrolidinylmethyl)phenols (ProPhenols), and the desired products are obtained in good yields (up to 88%) and with high stereoselectivity (up to > 99% ee and up to > 99:1 dr). This reaction also can be run on a gram scale without impacting its enantioselectivity.

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“…As exemplified above (Scheme 23), the hypothesized enolate intermediate produced in the radical conjugate addition promoted by a MHAT process could be engaged in sequential reactions, offering a range of possibilities for the design of new hydroalkylation cascades. In 2016, the Cui group reported the hydroalkylation of olefins 59 using p-quinone methides 60 as electrophilic partners (Scheme 24A) [91]. Alkenyl alcohols could be employed without needing to protect the hydroxy functional group, and the acidity of the phenolic hydrogen present in the product was also compatible with the reaction Scheme 23: Examples of cascade reactions triggered by HAT for the construction of trans-decalin backbone unities (highlighted in blue) in the total synthesis of natural products.…”

Section: Carbon-centered Radical Additions Via Metal Hydride Hydrogen H Atom Transfermentioning

confidence: 99%

Methodologies for the synthesis of quaternary carbon centers via hydroalkylation of unactivated olefins: twenty years of advances

Silva¹,

Coelho²

2021

Beilstein J. Org. Chem.

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Olefin double-bond functionalization has been established as an excellent strategy for the construction of elaborate molecules. In particular, the hydroalkylation of olefins represents a straightforward strategy for the synthesis of new C(sp3)–C(sp3) bonds, with concomitant formation of challenging quaternary carbon centers. In the last 20 years, numerous hydroalkylation methodologies have emerged that have explored the diverse reactivity patterns of the olefin double bond. This review presents examples of olefins acting as electrophilic partners when coordinated with electrophilic transition-metal complexes or, in more recent approaches, when used as precursors of nucleophilic radical species in metal hydride hydrogen atom transfer reactions. This unique reactivity, combined with the wide availability of olefins as starting materials and the success reported in the construction of all-carbon C(sp3) quaternary centers, makes hydroalkylation reactions an ideal platform for the synthesis of molecules with increased molecular complexity.

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Fe-Catalyzed Hydroalkylation of Olefins with para-Quinone Methides

Cited by 131 publications

References 51 publications

Mn-, Fe-, and Co-Catalyzed Radical Hydrofunctionalizations of Olefins

Mn-, Fe-, and Co-Catalyzed Radical Hydrofunctionalizations of Olefins

Asymmetric 1,6‐Conjugate Addition of para‐Quinone Methides for the Synthesis of Chiral β,β‐Diaryl‐α‐Hydroxy Ketones

Methodologies for the synthesis of quaternary carbon centers via hydroalkylation of unactivated olefins: twenty years of advances

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