Palladium-catalyzed ortho-alkenylation of aryl hydrogen phosphates using a new mono-phosphoric acid directing group

Chan, Li Yan; Kim, Sunggak; Ryu, Taekyu; Lee, Phil Ho

doi:10.1039/c3cc41107a

Cited by 90 publications

(20 citation statements)

References 76 publications

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“…In 2013, Kim, Lee, and co‐workers reported the highly efficient Pd II ‐catalyzed ortho ‐alkenylation and acetoxylation of phenols with olefins and [bis(acetoxy)iodo]benzene [PhI(OAc) 2 ] directed by a monophosphoric acid group (Scheme ). Both methods provided excellent regioselectivity and functional group tolerance.…”

Section: Ortho‐c−h Activation Of Phenolsmentioning

confidence: 99%

Transition Metal‐Catalyzed Directing‐Group‐Assisted C−H Activation of Phenols

Luo

2019

ChemSusChem

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Strategies that exploit directing groups to control the site selectivity in the C−H activation of arenes have received much attention during the past two decades. In light of the importance of phenol derivatives in the areas of pharmaceuticals, agrochemicals, and materials science, transition‐metal‐catalyzed C−H activation of phenols has proven to be an extremely useful tool in organic synthesis. This Minireview summarizes the current state‐of‐the‐art direct C−H activation of phenol derivatives under transition‐metal catalysis.

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Section: Ortho‐c−h Activation Of Phenolsmentioning

confidence: 99%

Transition Metal‐Catalyzed Directing‐Group‐Assisted C−H Activation of Phenols

Luo

2019

ChemSusChem

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“…31 Subsequently, phosphoric acid was used as a directing group by Kim, Lee, and co-workers [Scheme 12 (b)]. 32 The effectiveness of this directing group was utilized in phenol substrates giving products such as 28 and the scope of the reaction was demonstrated with different olefin partners. In 2013, Yang and co-workers reported the palladium-catalyzed C-H olefination of biaryls with phosphine oxide as the directing group to give products such as 29 [Scheme 12 (c)].…”

Section: Scheme 11 Hydroxyl-group-directed Ortho-c-h Bond Alkenylationmentioning

confidence: 99%

Palladium-Catalyzed Olefination of Aryl C–H Bonds by Using Directing Scaffolds

Bag

Maiti

2016

Synthesis

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Site selective C-H bond activation/C-C bond formation is an ideal target for organic chemists owing to the ubiquitous nature of C-H bonds in natural products. A particular aryl C-H bond can be predictably activated by a directing group. However, the majority of strong and weak coordinating directing groups have been implemented for ortho-C-H bond activation/C-alkenylation. More recently, meta-C-H functionalization has been promoted by fine-tuning directing templates. In this short review, we have summarized recent progress in palladium-catalyzed directing group/template-assisted ortho/meta-C-H olefination. 1 Introduction 2 Proximal C-H Olefination 3 Distal C-H Olefination 4 Conclusions Key words palladium, directing groups, olefination, ortho/meta-C-H bond, removable auxiliary Sukdev Bag (left) received his B.Sc. degree in chemistry from West Bengal State University in 2011. He obtained his M.Sc. degree from IIT Bombay in 2013. He is now Ph.D. fellow in the research group of Prof. Debabrata Maiti at IIT Bombay. His research interests are in the area of metal-catalyzed C-H activation. Debabrata Maiti (right) received his Ph.D. from Johns Hopkins University (USA) in 2008 under the supervision of Prof. Kenneth D. Karlin. After postdoctoral studies at Massachusetts Institute of Technology (MIT) with Prof. Stephen L. Buchwald (2008-2010), he joined the Department of Chemistry of IIT Bombay in 2011. His research interests are focused on the development of new and sustainable synthetic methodologies.

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“…Encouraged by the developments of Pd-catalyzed diverse carbon-carbon and carbon-heteroatom bond forming reactions via the direct C−H activation [14,15], our co-authors including Cui and Wu et al reported a direct C-H functionalization of quinoline N-oxide(A, Scheme 2) with dimethyl H-phosphonate (B1, Scheme 2) to generate heteroaryl phosphonate [16] (G, Scheme 2) under metal-and external oxidant-free conditions. In this reaction, not only high efficiency can be obtained, but also practicality, environmental friendliness and atom economy can be featured.…”

Section: Introductionmentioning

confidence: 99%