Palladium-Catalyzed Direct Ortho C–O bond construction of Azobenzenes with Iodobenzene diacetate via C–H Activation

Fu, Xiaopan; Wei, Zhenjiang; Xia, Chengcai; Shen, Chao; Zhang, Pengfei; Yang, Yong; Wang, Kai; Zhang, Pengfei

doi:10.1007/s10562-016-1955-7

Cited by 12 publications

(10 citation statements)

References 63 publications

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“…A palladium-catalyzed ortho -C(sp 2 )–H acetoxylation of azobenzenes with PIDA in HFIP was also reported, where azo group served as a DG and PIDA served as a source for an acetoxy group (Scheme ). HFIP was identified as an essential solvent as solvents like AcOH, MeCN, DMF, DMSO, and EtOH only provided trace conversions.…”

Section: C–h Functionalization Reactionsmentioning

confidence: 99%

HFIP in Organic Synthesis

et al. 2022

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1,1,1,3,3,3-Hexafluoroisopropanol (HFIP) is a polar, strongly hydrogen bond-donating solvent that has found numerous uses in organic synthesis due to its ability to stabilize ionic species, transfer protons, and engage in a range of other intermolecular interactions. The use of this solvent has exponentially increased in the past decade and has become a solvent of choice in some areas, such as C–H functionalization chemistry. In this review, following a brief history of HFIP in organic synthesis and an overview of its physical properties, literature examples of organic reactions using HFIP as a solvent or an additive are presented, emphasizing the effect of solvent of each reaction.

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Section: C–h Functionalization Reactionsmentioning

confidence: 99%

HFIP in Organic Synthesis

et al. 2022

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“…Very recently, Fu et al proposed more standard and mild reaction conditions for ortho-acetoxylation of azobenzenes by using Pd(OAc) 2 and a stoichiometric amount of PIDA in hexafluoroisopropanol (HFIP) under air at 40 °C (Scheme 16). 23 The authors highlighted the important role played by HFIP. The latter contributed to shorten reaction time and to enhance reaction efficacy.…”

Section: Monofunctionalization Of Azobenzenesmentioning

confidence: 99%

Advances in Direct Metal-Catalyzed Functionalization of Azobenzenes

2018

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Azobenzenes are a unique class of compounds that originally aroused interest because of their exceptional photochromic properties. Selective reactions allowing the preparation of complex polysubstituted azo-based photoswitches, in a direct and efficient manner, have received considerable attention over the past few years. Among them, regio- and chemoselective C–H bond activation in the presence of a transition-metal catalyst has emerged as the most attractive and challenging strategy in the synthesis of sterically constrained azo compounds. This synthetic approach is currently an intensive research field for introducing functional and structural diversity from azobenzenes. This short review summarizes the recent advances in both ortho-functionalization of azobenzenes and the synthesis of azo-derived heterocycles based on transition-metal-catalyzed direct C–H bond activation. The substrate scope, limitation, reaction mechanism as well as additional applications are discussed.

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“…Our research group has been engaged in the research of azo compounds. [13][14][15][16] Herein, we report a method for the synthesis of (E)-1-(phenyldiazenyl)cyclohexyl benzoate, which can synthesize azo compounds in high yield by arylhydrazine oxidation (Scheme 1B).…”

Section: Introductionmentioning

confidence: 99%