Palladium-catalyzed one-pot phosphorylation of phenols mediated by sulfuryl fluoride

Zhang, Yiyuan; Chen, Wanting; Tan, Tingting; Gu, Yuang; Zhang, Shuning; Li, Jie; Wang, Yan; Hou, Wenhua; Yang, Guang; Ma, Peixiang; Xu, Hongtao

doi:10.1039/d1cc00769f

Cited by 22 publications

(27 citation statements)

References 66 publications

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“…Professor Sharpless in 2014 (Dong et al, 2014;Barrow et al, 2019), have already gained wide application in the synthesis of drug screening libraries (Kitamura et al, 2020;Smedley et al, 2020), late-stage modification of drugs and natural products (Li S. et al, 2017;Liu et al, 2018), DNA-encoded library synthesis (Liu et al, 2019;Xu H. et al, 2019;Zhang et al, 2021), and the synthesis of 18 F radio tracers (Zheng et al, 2021).…”

Section: Sufex Chemistry Another Ideal Click Reaction Proposed Bymentioning

confidence: 99%

“…Today several elegant click chemistries have been well developed, such as strain-promoted azide-alkyne cycloaddition (SPAAC), inverse electron-demanded Diels-Alder (IEED-DA), and Sulfur (VI) Fluoride Exchange (SuFEx) chemistry. These chemistries have played a key in chemical biology and drug discovery, particularly the emerging SuFEx chemistry, another ideal click reaction proposed by Professor Sharpless in 2014 ( Dong et al, 2014 ; Barrow et al, 2019 ), have already gained wide application in the synthesis of drug screening libraries ( Kitamura et al, 2020 ; Smedley et al, 2020 ), late-stage modification of drugs and natural products ( Li S. et al, 2017 ; Liu et al, 2018 ), DNA-encoded library synthesis ( Liu et al, 2019 ; Xu H. et al, 2019 ; Zhang et al, 2021 ), and the synthesis of 18 F radio tracers ( Zheng et al, 2021 ).…”

Section: Introductionmentioning

confidence: 99%

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Click Chemistry in Natural Product Modification

Zhang

Zhao

et al. 2021

Front. Chem.

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Click chemistry is perhaps the most powerful synthetic toolbox that can efficiently access the molecular diversity and unique functions of complex natural products up to now. It enables the ready synthesis of diverse sets of natural product derivatives either for the optimization of their drawbacks or for the construction of natural product-like drug screening libraries. This paper showcases the state-of-the-art development of click chemistry in natural product modification and summarizes the pharmacological activities of the active derivatives as well as the mechanism of action. The aim of this paper is to gain a deep understanding of the fruitful achievements and to provide perspectives, trends, and directions regarding further research in natural product medicinal chemistry.

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Section: Sufex Chemistry Another Ideal Click Reaction Proposed Bymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Click Chemistry in Natural Product Modification

Zhang

Zhao

et al. 2021

Front. Chem.

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“…[ 59 ] The C(sp 2 )‐hetero (N, O, and S) bonds are traditionally constructed mainly through transition‐metal‐catalyzed cross‐coupling reactions. Up to now, although the metal‐catalyzed version of on‐DNA C(sp 2 )‐hetero bonds formation have elegantly developed by Lu, [ 60 ] Berst, [ 61 ] Torrado, [ 62 ] Simmons, [ 63 ] Dawson, [ 55 ] Chen, [ 64 ] Liu, [ 65 ] Pentelute [ 66 ] and their coworkers as well as our group, [ 26 , 32 , 67 ] the coupling partners are still limited to amines or thiophenols that are highly nucleophilic. For phenolic substrates, the inherently weak nucleophilic activity endows them with poor reactivity in the O ‐arylation reaction.…”

Section: Introductionmentioning

confidence: 99%

Metal‐Free and Open‐Air Arylation Reactions of Diaryliodonium Salts for DNA‐Encoded Library Synthesis

Tan

Zhang

et al. 2022

Advanced Science

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A successful DNA‐encoded library (DEL) will consist of diverse skeletons and cover chemical space as comprehensive as possible to fully realize its potential in drug discovery and chemical biology. However, the lack of versatile on‐DNA arylation methods for phenols that are less nucleophilic and reactive poses a great hurdle for DEL to include diaryl ether, a privileged chemotype in pharmaceuticals and natural products. This work describes the use of “substrate activation” approach to address the arylation of DNA‐conjugated phenols. Diaryliodonium salt, a highly electrophilic and reactive arylation reagent, is employed as Ar+ sources to ensure highly selective on‐DNA arylation of phenols and oximes with both high yields and DNA fidelity. Notably, the new on‐DNA arylation reaction can be applied to the late‐stage modification of peptides containing tyrosine side‐chain and to synthesize DNA‐tagged analogues of existing drug molecules such as sorafenib, a known pan‐kinase inhibitor. The new on‐DNA diaryliodonium salts chemistry affords a greater flexibility in DEL design and synthesis.

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“…Transformations at 110 °C and a reaction time of 18 h gave a wide range of phosphonate esters in high yields. Recently, the Ding and Xu groups independently reported Pd-catalyzed C–P bond-forming reactions of aryl fluorosulfonates . Following synthesis of these from phenols and sulfuryl fluoride gas, these compounds were readily coupled with a range of P(O)–H compounds using Pd(OAc) 2 and either dppf or DPEPhos ligands.…”

Section: Introductionmentioning

confidence: 99%

Palladium-Catalyzed C–P Bond-Forming Reactions of Aryl Nonaflates Accelerated by Iodide

2021

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An iodide-accelerated, palladium-catalyzed C–P bond-forming reaction of aryl nonaflates is described. The protocol was optimized for the synthesis of aryl phosphine oxides and was found to be tolerant of a wide range of aryl nonaflates. The general nature of this transformation was established with coupling to other P(O)H compounds for the synthesis of aryl phosphonates and an aryl phosphinate. The straightforward synthesis of stable, isolable aryl nonaflates, in combination with the rapid C–P bond-forming reaction allows facile preparation of aryl phosphorus target compounds from readily available phenol starting materials. The synthetic utility of this general strategy was demonstrated with the efficient preparation of an organic light-emitting diode (OLED) material and a phosphonophenylalanine mimic.

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Palladium-catalyzed one-pot phosphorylation of phenols mediated by sulfuryl fluoride

Abstract: We report a general palladium-catalyzed one-pot procedure for the synthesis of phosphonates, phosphinates and phosphine oxides from phenols mediated by sulfuryl fluoride. It features mild conditions, broad substrate scope, high...

Cited by 22 publications

References 66 publications

Click Chemistry in Natural Product Modification

Click Chemistry in Natural Product Modification

Metal‐Free and Open‐Air Arylation Reactions of Diaryliodonium Salts for DNA‐Encoded Library Synthesis

Palladium-Catalyzed C–P Bond-Forming Reactions of Aryl Nonaflates Accelerated by Iodide

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