Palladium catalyzed desulfinylative couplings between aryl sulfinates and aryl bromide/iodide for the synthesis of biaryls

Gund, Sitaram Haribhau; Balsane, Kishor Eknath; Nagarkar, Jayashree M.

doi:10.1016/j.tet.2016.05.081

Cited by 12 publications

(7 citation statements)

References 59 publications

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“…The procedure yielded 1.06 g (66 %) of the title compound as a white solid. Spectral data is consistent with the literature [50] . 1 H NMR (400 MHz, CDCl 3 ) δ 7.63 (dd, J =8.2, 1.3 Hz, 2H), 7.43 – 7.27 (m, 5H), 7.09 (dd, J =5.1, 3.6 Hz, 1H).…”

Section: Methodssupporting

confidence: 91%

Metal‐Free Transfer C−H Borylation of Substituted Thiophenes

Fontaine

Desrosiers

Gaudy

et al. 2023

Zeitschrift anorg allge chemie

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Thiophenes are crucial chemical building blocks in the fields of medicinal and material chemistry. As such, the CÀ H functionalization of these units is of key importance for developing novel applications. Herein, we report the CÀ H borylation of thiophenes using metal-free transfer CÀ H borylation. When performed on C2-substituted thiophenes, the reaction is selective for the borylation on C5, while C3-substituted thiophenes are borylated on C2, a complementary selectivity from reported CÀ H borylation approaches that typically prefer to borylate at the C5 position. An optimization of the catalytic system was performed. The reaction was shown to work with electronically diverse thiophenes and was also compatible with sensitive functional groups. Computational investigation of the reaction mechanism suggests a Lewis pair CÀ H activation mechanism with a selectivity that is kinetically driven. The methodology developed herein is an economical pathway for the preparation of C2-borylated C3-substituted thiophenes.

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Section: Methodssupporting

confidence: 91%

Metal‐Free Transfer C−H Borylation of Substituted Thiophenes

Fontaine

Desrosiers

Gaudy

et al. 2023

Zeitschrift anorg allge chemie

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“…Pd (II)-phosphine ligand systems were first examined on the basis of several recent reports. [43,44] However, the PdCl 2 /P (OPh) 3 -catalyzed reaction using tetrabutylammonium iodide (TBAI) as the additive and KOAc as the base in dimethylsulfoxide (DMSO) at 100°C gave only a trace amount of cross-coupling product ( Table 1, entry 1). The screening of monodentate phosphine-based ligands, such as PCy 3 , TFP (trifurylphosphine) and Xphos (2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl), gave SCHEME 1 Palladium-catalyzed denitrogenative and desulfinative cross-coupling of arylsulfonyl hydrazides [13][14][15].…”

Section: Resultsmentioning

confidence: 99%

Desulfinative and denitrogenative palladium‐catalyzed cross‐coupling of arylsulfonyl hydrazides with aryl diazonium salts

Shang

2018

Applied Organom Chemis

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Palladium-catalyzed cross-coupling of arylsulfonyl hydrazides with aryl diazonium salts to provide biaryl products under relatively mild conditions is established. This reaction proceeded smoothly with tetrabutylammonium iodide and gave the corresponding products with C-C bonds formed using PdCl 2 /bis (dicyclohexylphosphino) methane catalyst under air. This method also allowed easy access to significant functional biaryls for potential applications in medicinal and organic chemistry.

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“…Recently, aryl−aryl bond formation via C−S bond cleavage has attracted considerable attention, and versatile activated C−S bond‐containing partners, such as aryl sulfonyl reagents, have been explored in cross‐coupling reactions under transition metal catalysis. Commercial aryl sulfonyl halides, sulfinates and hydrazines are recognized as the new aryl sources that have been universally utilized in desulfinative arylation reactions recently (Scheme ) …”

Section: Introductionmentioning

confidence: 99%

“…Recently, aryl−aryl bond formation via C−S bond cleavage has attracted considerable attention, and versatile activated C−S bond-containing partners, such as aryl sulfonyl reagents, have been explored in cross-coupling reactions under transition metal catalysis. Commercial aryl sulfonyl halides, [5,[34][35][36] sulfinates [37][38][39][40][41][42] and hydrazines [42][43][44][45][46][47][48][49][50][51] are recognized as the new aryl sources that have been universally utilized in desulfinative arylation reactions recently (Scheme 1). [52][53][54] As we all known, arylsulfonyl hydrazides are relatively stable, simple to handle and easy to prepare from their corresponding sulfonyl chlorides.…”

mentioning

confidence: 99%

Desulfinative palladium‐catalyzed cross‐coupling of arylsulfonyl hydrazides with aryl bromides under air

Liu

Yang

2019

Applied Organom Chemis

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A highly efficient and mild palladium‐catalyzed cross‐coupling of arylsulfonyl hydrazides and aryl bromides for the selective synthesis of unsymmetrical biaryls has been developed. This methodology has the advantages of easily accessible starting materials, functional group tolerance and a wide range of substrates, which provide rapid access to biaryls derivatives. In this protocol, abundant and stable aryl bromides serve as the aryl sources by coupling reaction of the aryl group generated from arylsulfonyl hydrazides via in situ release of nitrogen and sulfur dioxide. No external oxidants or acids are needed for this kind of transformation.

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Palladium catalyzed desulfinylative couplings between aryl sulfinates and aryl bromide/iodide for the synthesis of biaryls

Cited by 12 publications

References 59 publications

Metal‐Free Transfer C−H Borylation of Substituted Thiophenes

Metal‐Free Transfer C−H Borylation of Substituted Thiophenes

Desulfinative and denitrogenative palladium‐catalyzed cross‐coupling of arylsulfonyl hydrazides with aryl diazonium salts

Desulfinative palladium‐catalyzed cross‐coupling of arylsulfonyl hydrazides with aryl bromides under air

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