Sterically demanding aryl–alkyl Suzuki–Miyaura coupling

Li, Chengxi; Xiao, Guolan; Zhao, Qing; Liu, Huimin; Wang, Tao; Tang, Wenjun

doi:10.1039/c4qo00024b

Cited by 42 publications

(15 citation statements)

References 43 publications

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“…In Li and Wu's work, a catalyst‐free aminosulfonylation was developed through insertion of sulfur dioxide with aryl/alkyl halides enabled by photoenergy . Under ultraviolet irradiation, the three‐component reaction between aryl/alkyl halides 70 , sulfur dioxide, and hydrazines 71 proceeds smoothly constructing a C–S–N skeleton under mild conditions without a metal or photoredox catalyst.…”

Section: Sulfonylationmentioning

confidence: 99%

Photoredox Catalysis in C–S Bond Construction: Recent Progress in Photo‐Catalyzed Formation of Sulfones and Sulfoxides

et al. 2017

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The emergence of radical chemistry as well as green chemistry in organic synthesis has initiated an interest in photochemistry over the past decade. With catalytic amounts of photoredox catalysts under light irradiation, high active radical species are produced, which could trigger the subsequent organic transformations smoothly. Among the various photoredox reactions, photo‐catalytic C–S bond formation continues to thrive, as the C–S bond is indispensable in many important biological and pharmaceutical compounds. Great attention has been devoted to this area as illustrated by the series of papers on sulfone and sulfoxide skeleton synthesis under irradiation published in the past years. This review summarizing the recent advances in photo‐catalyzed sulfones and sulfoxide formation is arranged by reaction type together with the sulfur source covering sulfonylation and sulfinylation reactions. It is intended to provide readers with a comprehensive understanding of photo‐catalytic C‐S bond formation and offer help for future research.

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Section: Sulfonylationmentioning

confidence: 99%

Photoredox Catalysis in C–S Bond Construction: Recent Progress in Photo‐Catalyzed Formation of Sulfones and Sulfoxides

et al. 2017

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“…In 2014, Tang et al revealed a sterically demanding aryl-alkyl SMC between di-ortho-substituted arylhalides 79 and (secondary) cycloalkylboronic acids 78 using a highly reactive Pd-AntPhos catalyst that allowed to reduce the β-hydride elimination (Scheme 12D). The method comprised a scope of sterically hindered substituted aryl compounds, including highly substituted benzene, naphthalene and anthracene derivatives [115]. The same group described the cross-coupling between aryl/alkenyl triflates 82 and acyclic secondary alkylboronic acids 81 in good The progress of utilizing alkylboronic acids was reviewed in 2008 [110].…”

Section: Scheme 12 Alkylboronic Acids As Coupling Partners In Sp 3 -mentioning

confidence: 99%

Recent Advances in Metal-Catalyzed Alkyl–Boron (C(sp3)–C(sp2)) Suzuki-Miyaura Cross-Couplings

El‐Maiss

Dine

et al. 2020

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Boron chemistry has evolved to become one of the most diverse and applied fields in organic synthesis and catalysis. Various valuable reactions such as hydroborylations and Suzuki–Miyaura cross-couplings (SMCs) are now considered as indispensable methods in the synthetic toolbox of researchers in academia and industry. The development of novel sterically- and electronically-demanding C(sp3)–Boron reagents and their subsequent metal-catalyzed cross-couplings attracts strong attention and serves in turn to expedite the wheel of innovative applications of otherwise challenging organic adducts in different fields. This review describes the significant progress in the utilization of classical and novel C(sp3)–B reagents (9-BBN and 9-MeO-9-BBN, trifluoroboronates, alkylboranes, alkylboronic acids, MIDA, etc.) as coupling partners in challenging metal-catalyzed C(sp3)–C(sp2) cross-coupling reactions, such as B-alkyl SMCs after 2001.

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“…Transition metal complexes of phosphorous (P), nitrogen (N), sulphur (S), and oxygen (O)-based ligands and their hybrids have provided chemists with a wide opportunity and a quasi-exhaustive tool for creating C-C bonds of significant interest [1,2]. The reactivity and the catalytic behaviour of these complexes largely depend on the nature of the coordinating atoms, their relative position within the molecular architecture, and the relative flexibility or rigidity of the ligand backbone, as they greatly influence steric and electronic properties of the resulting complex [3,4]. Therefore, the fine-tuning of these properties in order to synthesize ligands of particular interest has been an interesting strategy.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Mono- and Bis-Pyrazoles Bearing Flexible p-Tolyl Ether and Rigid Xanthene Backbones, and Their Potential as Ligands in the Pd-Catalysed Suzuki–Miyaura Cross-Coupling Reaction

et al. 2019

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The present work describes the synthesis of mono- and bis-pyrazole compounds bearing flexible p-tolyl ether and rigid 4,5-dibromo-2,7-di-tert-butyl-9,9-dimethyl-9H-xanthene backbones as pyrazolyl analogues of DPEphos and Xantphos ligands, respectively. The synthesis of new pyrazolyl analogues was accomplished following an Ullmann coupling protocol, and the resulting products were isolated in overall good yields. In addition, a hybrid imidazolyl–pyrazolyl analogue bearing a xanthene backbone was synthesized using the same protocol, whereas a hybrid selanyl–pyrazolyl analogue with a xanthene backbone was synthesized in a good yield employing a second C–H activation step. The symmetrical bis-pyrazolyl and the hybrid imidazolyl–pyrazolyl analogues were found to be the most active among the new ligands evaluated in the Pd-catalysed Suzuki-Miyaura cross-coupling of aryl halides with aryl boronic acids. A simple catalytic system based on Pd(OAc)2/2a was developed, which efficiently catalyses the Suzuki–Miyaura reaction of aryl halides and aryl boronic acids and provides moderate to excellent yields of the corresponding cross-coupling products.

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Sterically demanding aryl–alkyl Suzuki–Miyaura coupling

Abstract: Efficient sterically demanding aryl–alkyl Suzuki–Miyaura coupling between di-ortho-substituted aryl halides and secondary alkylboronic acids has been achieved with a Pd-AntPhos catalyst.

Cited by 42 publications

References 43 publications

Photoredox Catalysis in C–S Bond Construction: Recent Progress in Photo‐Catalyzed Formation of Sulfones and Sulfoxides

Photoredox Catalysis in C–S Bond Construction: Recent Progress in Photo‐Catalyzed Formation of Sulfones and Sulfoxides

Recent Advances in Metal-Catalyzed Alkyl–Boron (C(sp3)–C(sp2)) Suzuki-Miyaura Cross-Couplings

Synthesis of Mono- and Bis-Pyrazoles Bearing Flexible p-Tolyl Ether and Rigid Xanthene Backbones, and Their Potential as Ligands in the Pd-Catalysed Suzuki–Miyaura Cross-Coupling Reaction

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