Pd‐Catalyzed C−H Arylation of Benzothiazoles with Diaryliodonium Salt: One‐Pot Synthesis of 2‐Arylbenzothiazoles

Yang, Peng; Wang, Rui; Wu, Hui; Du, Zhengyin; Fu, Ying

doi:10.1002/ajoc.201600514

Cited by 14 publications

(10 citation statements)

References 70 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Since 2-arylbenzothiazole derivatives are attractive building blocks for various drug molecules, their synthesis via a palladium-catalyzed C-H arylation in the presence of diaryliodonium salts has been developed [76,85]. The reactions are catalyzed by palladium bromide in the presence of cesium carbonate and 1,3-bis(diphenyphosphino)propane (dppp) as a ligand and are conducted at reflux in acetonitrile for 24 h (Scheme 17a).…”

Section: Introductionmentioning

confidence: 99%

Diaryliodoniums Salts as Coupling Partners for Transition-Metal Catalyzed C- and N-Arylation of Heteroarenes

2020

View full text Add to dashboard Cite

Owing to the pioneering works performed on the metal-catalyzed sp2 C–H arylation of indole and pyrrole by Sanford and Gaunt, N– and C-arylation involving diaryliodonium salts offers an attractive complementary strategy for the late-stage diversification of heteroarenes. The main feature of this expanding methodology is the selective incorporation of structural diversity into complex molecules which usually have several C–H bonds and/or N–H bonds with high tolerance to functional groups and under mild conditions. This review summarizes the main recent achievements reported in transition-metal-catalyzed N– and/or C–H arylation of heteroarenes using acyclic diaryliodonium salts as coupling partners.

show abstract

Section: Introductionmentioning

confidence: 99%

Diaryliodoniums Salts as Coupling Partners for Transition-Metal Catalyzed C- and N-Arylation of Heteroarenes

2020

View full text Add to dashboard Cite

show abstract

“…Beginning from known bromide X [ 27 ], palladium-catalysed borylation provided either BE01 or BE02 in a single step in good yields ( figure 1 d ). Thereafter, treatment with trimethyloxonium tetrafluoroborate (Meerwein's salt) provided the corresponding N -methylbenzothiazolium dyes mBE01 and mBE02.…”

Section: Resultsmentioning

confidence: 99%

Bifunctional fluorescent probes for detection of amyloid aggregates and reactive oxygen species

et al. 2018

View full text Add to dashboard Cite

Protein aggregation into amyloid deposits and oxidative stress are key features of many neurodegenerative disorders including Parkinson's and Alzheimer's disease. We report here the creation of four highly sensitive bifunctional fluorescent probes, capable of H 2 O 2 and/or amyloid aggregate detection. These bifunctional sensors use a benzothiazole core for amyloid localization and boronic ester oxidation to specifically detect H 2 O 2 . We characterized the optical properties of these probes using both bulk fluorescence measurements and single-aggregate fluorescence imaging, and quantify changes in their fluorescence properties upon addition of amyloid aggregates of α-synuclein and pathophysiological H 2 O 2 concentrations. Our results indicate these new probes will be useful to detect and monitor neurodegenerative disease.

show abstract

“…Finally, a possible reaction mechanism for Cu-catalyzed 有机化学研究论文 direct arylation of benzothiazoles with diaryliodonium salts was proposed based on our experimental observations and previous literatures (Scheme 2). [19,[21][22] An initial cupration of benzothiazole (1a) with CuI in the presence of Cs 2 CO 3 affords thiazolyl-copper species I. Subsequent oxidative addition of I to diphenyliodonium tetrafluoroborate delivers to an electrophilic Cu(III)-aryl species II with the removal of iodobenzene.…”

Section: Resultsmentioning

confidence: 99%

“…[14][15][16][17][18] With continuous research interests in C-H activation and functionalization, some transition metal-catalyzed C-H arylation protocols of aromatics and heteroaromatics by using diaryliodonium salts and aryl halides as coupling partners were developed and good results were obtained. [19][20][21] Herein, a copper-catalyzed direct C-H arylation of benzothiazoles with diaryliodonium salts as arylating reagents (Scheme 1) is reported. It is a simple, cheap and efficient method to synthesize 2-arylbenzothiazole derivatives.…”

Section: Introductionmentioning

confidence: 99%

Cu-Catalyzed Direct Arylation of Benzothiazoles with Diaryliodonium Salts

Li¹,

Yang²,

Xu³

et al. 2020

Chin. J. Org. Chem.

Self Cite

View full text Add to dashboard Cite

Diaryliodonium salts have low toxicity and good stability, and their mediated reactions often have advantages of mild reaction conditions and high selectivity. They have received extensive attention and have been widely used as arylating agents in organic synthesis. A simple and efficient method for the synthesis of 2-arylbenzothiazole derivatives via copper-catalyzed C-H direct arylation of benzothiazoles with diaryliodonium salts as electrophilic arylating reagents was developed. This method shows wide range of substrates, good group tolerance, simple operation and high product yields.

show abstract

Pd‐Catalyzed C−H Arylation of Benzothiazoles with Diaryliodonium Salt: One‐Pot Synthesis of 2‐Arylbenzothiazoles

Cited by 14 publications

References 70 publications

Diaryliodoniums Salts as Coupling Partners for Transition-Metal Catalyzed C- and N-Arylation of Heteroarenes

Diaryliodoniums Salts as Coupling Partners for Transition-Metal Catalyzed C- and N-Arylation of Heteroarenes

Bifunctional fluorescent probes for detection of amyloid aggregates and reactive oxygen species

Cu-Catalyzed Direct Arylation of Benzothiazoles with Diaryliodonium Salts

Contact Info

Product

Resources

About