Palladium-Catalyzed Tandem Reaction of Three Aryl Iodides Involving Triple C–H Activation

Luo, Xiai; Xu, Yankun; Xiao, Genhua; Liu, Wenjuan; Qian, Cheng; Deng, Guobo; Song, Jianxin; Liang, Yun; Yang, Chunming

doi:10.1021/acs.orglett.8b00982

Cited by 47 publications

(19 citation statements)

References 78 publications

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“…14 Yang and Liang have applied this strategy for oxindole synthesis, and two aryl groups derived from 28 were incorporated in the final products. 15 In their subsequent study, Lautens and co-workers found that intermediate 26 could be trapped by Me 6 Si 2 or Me 6 Ge 2 , thus disilylation or digermanylation of 23 could be easily realized. 16a Shortly after this study, Liang and Yang reported a palladium-catalyzed domino Heck-disilylation and borylation of alkenetethered 2-(2-halophenyl)-1H-indoles.…”

Section: Short Review Synthesismentioning

confidence: 99%

Recent Advances in Palladium-Catalyzed Bridging C–H Activation by Using Alkenes, Alkynes or Diazo Compounds as Bridging Reagents

et al. 2020

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Transition-metal-catalyzed direct inert C–H bond functionalization has attracted much attention over the past decades. However, because of the high strain energy of the suspected palladacycle generated via C–H bond palladation, direct functionalization of a C–H bond less than a three-bond distance from a catalyst center is highly challenging. In this short review, we summarize the advances on palladium-catalyzed bridging C–H activation, in which an inert proximal C–H bond palladation is promoted by the elementary step of migratory insertion of an alkene, an alkyne or a metal carbene intermediate.1 Introduction2 Palladium-Catalyzed Alkene Bridging C–H Activation2.1 Intramolecular Reactions2.2 Intermolecular Reactions3 Palladium-Catalyzed Alkyne Bridging C–H Activation3.1 Intermolecular Reactions3.2 Intramolecular Reactions4 Palladium-Catalyzed Carbene Bridging C–H Activation5 Conclusion and Outlook

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Section: Short Review Synthesismentioning

confidence: 99%

Recent Advances in Palladium-Catalyzed Bridging C–H Activation by Using Alkenes, Alkynes or Diazo Compounds as Bridging Reagents

et al. 2020

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“…343 These works were followed by Liang and Yang's report on the synthesis of 109 in a triple C-H activation approach where the alkylPd II intermediate is intercepted by 2 further equivalents of aryl iodide (Scheme 69). 344 Another approach is Pd-catalysed migratory insertion of diazo compounds and Michael addition. 345 Chiral hypervalent iodine mediated.…”

Section: Spirocylohexanyl Oxindolesmentioning

confidence: 99%

Stereoselective synthesis and applications of spirocyclic oxindoles

2021

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“…In the first case, the migratory insertion of unsaturated coupling partners, such as alkynes, arynes, diazocompounds or even fullerenes, into the Pd-C bond of intermediates 122 lead to spirocyclic scaffolds I (Scheme 96). [107a,125] In those cascade reactions where the coupling partner (such as TMS-TMS, [120d] CH 2 Br 2 [126] or haloarenes, [127] among others [128] ) can add oxidatively to the Pd(II) center in 122 to give the Pd(IV) species 123, a variety of functionalized organic products II can be obtained.…”

Section: Selected Examples Of Catalytic Reactions Involving Cc-palladacyclic Intermediatesmentioning

confidence: 99%

Chasing C,C‐Palladacycles

Garcı́a-López

Saura‐Llamas

2021

Eur J Inorg Chem

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The different approaches for the synthesis of C,C-palladacycles are reviewed in this manuscript. These species hold a bidentate ligand that chelates the Pd atom through two C-donor moieties. Their relevance is closely related to the fact that they are intermediates in many palladium-catalyzed transformations. Furthermore, some of them have been used as efficient catalyst in cross coupling reactions. The review is structured according to the different strategies that have been employed to achieve the synthesis of the C,C-palladacycle derivatives, starting with those involving one elemental step (such as the oxidative addition of strained CÀ C bonds to Pd(0) or the transmetalation reactions between organometallic reagents and Pd(II) precursors), and continuing with more complex processes, where at least two elementary steps of Pd chemistry are involved (for example, carbometalation of alkenes followed by a CÀ H activation process). A final section highlights some aspects of synthetic methodologies based on Pd catalysis in which one or several C,C-palladacyclic intermediates are involved.Lenarda et al. synthesized the first reported four-membered C,C-palladacycles 1 a and 1 b in 1972, [5] via the oxidative addition of 1,1,2,2-tetracyanocyclopropane to [Pd(PPh 2 R) 4 ] (R = Ph; Me) (Scheme 1). The reaction occurred with the CÀ C bond cleavage of the highly strained ring and oxidative addition of the two resulting fragments to Pd(0).

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Palladium-Catalyzed Tandem Reaction of Three Aryl Iodides Involving Triple C–H Activation

Cited by 47 publications

References 78 publications

Recent Advances in Palladium-Catalyzed Bridging C–H Activation by Using Alkenes, Alkynes or Diazo Compounds as Bridging Reagents

Recent Advances in Palladium-Catalyzed Bridging C–H Activation by Using Alkenes, Alkynes or Diazo Compounds as Bridging Reagents

Stereoselective synthesis and applications of spirocyclic oxindoles

Chasing C,C‐Palladacycles

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