Palladium(II)-Catalyzed C–H Bond Activation/C–C Coupling/Intramolecular Tsuji–Trost Reaction Cascade: Facile Access to 2<i>H</i>-Pyranonaphthoquinones

Bian, Jinlei; Xue, Qunji; Wang, Nan; Mu, Tong; Li, Xiang; Sun, Haopeng; Zhang, Lianshan; You, Qidong; Zhang, Xiaojin

doi:10.1021/acs.orglett.5b01304

Cited by 21 publications

(7 citation statements)

References 27 publications

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“…[19f] Zhang group demonstrated the synthesis of 2H-pyranonaphthoquinones 80 (45-88 % yield) from readily accessible hydroxynaphthoquinone 78 and alkenyl carbonate 79 via a carbopalladation/Tsuji À Trost reaction cascade (Scheme 11). [20] Chang et al developed a protocol involving aerobic Wackertype oxidation/intramolecular aldol cyclization to construct functionalized naphthols 82 (69-88 % yield) and benzofurans 83 (72-76 % yield). This strategy could be extended for the isocoumarins and 1,5-dicarbonyl compounds as well.…”

Section: Cascade Reactions Involving Wacker-type Reactivitymentioning

confidence: 99%

Exploiting the Versatility of Palladium Catalysis: A Modern Toolbox for Cascade Reactions

et al. 2021

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Dedicated to Professor S. Chandrasekaran on the occasion of his 75 th birthday.Palladium-catalyzed cascade cyclization received much attention in organic synthesis due to its efficiency and rapid transformation of simple starting materials into complex molecular skeletons. Celebrating the 10 th year of the prestigious Nobel prize for palladium chemistry, we witness it still proceeds strong over other transition metals for its versatility. Cascade reactions in contemporary organic synthesis reduced cost and time through careful design. It has emerged as the first choice, a powerful tool for multiple bond formations in one step with a wide range of functional group tolerance due to the deep understanding of various pathways. A variety of compounds with biological relevance with complex molecular scaffolds have been achieved using these cascade coupling reactions. This review outlines Pd-catalyzed cascade reactions from the post-Nobel era. Nevertheless, more discoveries and endless possibilities for new transformations are underway.

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Section: Cascade Reactions Involving Wacker-type Reactivitymentioning

confidence: 99%

Exploiting the Versatility of Palladium Catalysis: A Modern Toolbox for Cascade Reactions

et al. 2021

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“…For example, in 2015 Bian et al . disclosed a cascade strategy for the synthesis of 2 H ‐pyranonaphthoquinones by annulation of 2‐hydroxynaphthoquinones with allylic carbonates [78] . Oxidative insertion of Pd(II) into the quinoidal C−H bond, oxidative coupling with the allylic carbonate, then intramolecular Tsuji‐Trost reaction delivered the pyranonaphthoquinone product (Scheme 45).…”

Section: Quinone Substrate‐directed C−h Metalationmentioning

confidence: 99%

The Different Facets of Metal‐Catalyzed C−H Functionalization Involving Quinone Compounds

Wood

Carvalho

Júnior

2021

The Chemical Record

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Metal‐catalysed C−H functionalization has emerged as a powerful platform for the derivatization of quinones, a class of compounds with wide‐ranging applications. This review organises and discusses the evolution of this chemistry from early Fujiwara‐Moritani reactions, through to modern directing‐group assisted C−H functionalization processes, including C−H functionalization reactions directed by the quinone ring itself. Mechanistic details of these reactions are provided to afford insight into how the unique reactivity of quinoidal compounds has been leveraged in each example.

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“…Thes ynthesis of 2H-pyranonaphthoquinones 317 from 2-hydroxy-1,4-naphthoquinones 315 and allylic carbonates 316 was reported by Zhang et al in 2015 (Scheme 96). [143] Thea uthors propose an initiation via the coordination of the alkoxide to Pd(II) and subsequent C(sp 2 )-H activation. Thea lkenyl-Pd(II) species then undergoes an intermolecular Heck reaction, generatingt he hydroxy-1,4-naphthoquinone allyl carbonate 318 andP d(0) via the formation of acetic acid.…”

Section: Tsuji-trost-based Cascade Reactionsmentioning

confidence: 99%

Advances in Palladium‐Catalyzed Cascade Cyclizations

Biemolt

Ruijter

2018

Adv Synth Catal

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Thep ast decades in organic chemistry have witnessed significant improvements in synthetic efficiency as ar esult of considerable progress in cascade reactions,t andem reactions,a nd related onepot processes. These methods are less time-consuming andp roduce less waste comparedt ot he classical stepwise approach. However, cascade chemistry requires am ore careful design and compatible reaction types for success.P alladium-catalyzed cross-coupling reactions,w ith their well understoodm ultistep catalytic cycles,f orm ap romising basis for the design of cascade reactions.F urthermore,t hey are compatible with ar ange of functional groups and can be combined with ar ange of secondary transformations. Ther esulting palladium-catalyzed cascade reactions have provided access to ap lethorao fc omplex small molecules of high medicinal relevance.T his review providesa no verview of the developments in palladium-catalyzed cascade reactions since 2011, classified according to the initiation, propagation, andtermination steps comprising the palladium cascade reactions.T hisc lassification should assist the reader and may provide inspiration for the design of newc ascade reactions.

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Palladium(II)-Catalyzed C–H Bond Activation/C–C Coupling/Intramolecular Tsuji–Trost Reaction Cascade: Facile Access to 2H-Pyranonaphthoquinones

Cited by 21 publications

References 27 publications

Exploiting the Versatility of Palladium Catalysis: A Modern Toolbox for Cascade Reactions

Exploiting the Versatility of Palladium Catalysis: A Modern Toolbox for Cascade Reactions

The Different Facets of Metal‐Catalyzed C−H Functionalization Involving Quinone Compounds

Advances in Palladium‐Catalyzed Cascade Cyclizations

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