Ruthenium-Catalyzed Functionalization of Aryl Carbon−Oxygen Bonds in Aromatic Ethers with Organoboron Compounds

Kakiuchi, Fumitoshi; Usui, Mayumi; Ueno, Satoshi; Chatani, Naoto; Murai, Shinji

doi:10.1021/ja0393170

Cited by 245 publications

(103 citation statements)

References 10 publications

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“…31,33 In 2008, Chatani and Tobisu overcame such limitation by designing an elegant Ni-catalyzed SuzukiMiyaura coupling reaction of aryl methyl ethers with organoboron reagents (Scheme 18). 34 Practicality and novelty aside, such a method offered new vistas for the utilization of aryl methyl ethers in cross-coupling reactions, a field that has largely been dominated by the employment of highly reactive and air-sensitive Grignard reagents.…”

Section: Suzuki-miyaura Type Reactionsmentioning

confidence: 99%

Metal-catalyzed activation of ethers via C–O bond cleavage: a new strategy for molecular diversity

2014

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In 1979, the seminal work of Wenkert set the standards for the utilization of aryl and vinyl ethers as coupling partners via C-O bond-cleavage. Although the topic remained dormant for almost three decades, the last years have witnessed a renaissance in this area of expertise, experiencing an exponential growth and becoming a significant discipline within the cross-coupling arena. The means to utilize readily accessible aryl or vinyl ethers as counterparts does not only represent a practical, powerful and straightforward alternative to organic halides, but also constitutes an excellent opportunity to improve our chemical knowledge on a relative unexplored area of expertise. This review summarizes the most significant developments in the area of C-O bond-cleavage when employing aryl or vinyl ethers, providing a detailed overview of the current state of the art and including future aspects, when applicable.

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Section: Suzuki-miyaura Type Reactionsmentioning

confidence: 99%

Metal-catalyzed activation of ethers via C–O bond cleavage: a new strategy for molecular diversity

2014

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“…However, this breakthrough was overlooked for decades, until quite recently. After the development of improved conditions, ArOR can now be used as a coupling partner in several types of transition metal (TM)-catalyzed cross-couplings and related transformations, such as Suzuki-Miyaura-type (B), [24][25][26][27][28][29][30][31] Negishi-type (Zn or Al), [32][33][34][35][36] Murahashi-type (Li), [37][38][39][40] and other reactions. [41][42][43][44][45][46][47][48][49][50] As a continuation of our work in this area, we reported in 2012 the first ethereal Negishi-type coupling of aryl alkyl ether 36) (Chart 1(1)) and in 2016 we reported a systematic examination of ethereal Murahashi-type reaction 37) (Chart 1(2)).…”

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confidence: 99%

Ethereal C–O Bond Cleavage Mediated by Ni(0)-Ate Complex: A DFT Study

et al. 2017

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Density functional theory calculations were performed to explore the mechanism of Ni-catalyzed crosscoupling reactions involving organo-lithium and -zinc reagents through ethereal C-O bond cleavage. Based on this work, together with our previous mechanistic study on etheric Kumada-Tamao reaction, we identify and characterize a novel catalytic cycle for cross-coupling mediated by Ni(0)-ate complex.Key words cross-coupling; ether; nickel catalyst; organolithium; organozinc; density functional theory (DFT) calculation Efficient and selective cleavage and transformation of C-O bonds, particularly by means of cross-coupling methods, has attracted great interest, since compounds containing C-O moieties occur widely in nature and are also extensively utilized in industry.1-8) Among C-O compounds, ethers are particularly attractive, [1][2][3][4][5][6][7][8] as they offer the advantages of 1) high atom economy/conversion efficiency (the use of ethers as simple as MeO as substrates affords fewer by-products compared with tosylate, mesylate, triflate, phosphate, etc.), 2) environmental compatibility (cleavage of the C-O moiety in ether releases non-halogen-containing waste), and 3) excellent stability, easy accessibility and wide diversity. However, ethereal C-O bonds ( E C-O) are very unreactive, and most of the well-established Pd-catalyzed C-O bond-cleaving protocols are ineffective for ethers.On the other hand, Ni-catalysts have proved effective for many types of C-O bond cleavage, including ethers. As early as in 1979, Wenkert et al. 9,10) reported the first Ni-catalyzed Kumada-Tamao type (Mg) 9-23) reaction, in which aryl methyl ether (ArOMe) acted as the electrophilic partner, and this is now recognized as the first example of Ni-catalyzed activation of an inert C-O bond. However, this breakthrough was overlooked for decades, until quite recently. After the development of improved conditions, ArOR can now be used as a coupling partner in several types of transition metal (TM)-catalyzed cross-couplings and related transformations, such as Suzuki-Miyaura-type (B), [24][25][26][27][28][29][30][31] Negishi-type (Zn or Al), [32][33][34][35][36] Murahashi-type (Li), [37][38][39][40] and other reactions. 41-50) As a continuation of our work in this area, we reported in 2012 the first ethereal Negishi-type coupling of aryl alkyl ether 36) (Chart 1(1)) and in 2016 we reported a systematic examination of ethereal Murahashi-type reaction 37) (Chart 1(2)). More recently, we also reported an in-depth study of Ni-catalyzed cross-coupling between organoaluminums and various types of C-O electrophiles, including aryl alkyl ether. 32) Results and DiscussionThe conventional catalytic cycle for cross-coupling reaction consists of three elemental steps: oxidative addition (OA), transmetalation, and reductive elimination. [51][52][53][54] Martin and colleagues reported that direct OA of a E C-O bond to Ni(0) requires high temperature, based on experimental and theoretical findings.46) Computational studies by Nakamura and colleagues, ...

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“…Aryl methyl ethers, which are as readily available as aryl halides, have never been used in the Suzuki-Miyaura coupling reaction, except for the ruthenium-catalyzed system, [8] which requires a ligating group at the ortho position for the reaction to proceed. Herein, we describe a method for the nickel-catalyzed cross-coupling of aryl methyl ethers with boronic esters [Eq.…”

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confidence: 99%