Synthesis of Aryl Sulfonamides via Palladium-Catalyzed Chlorosulfonylation of Arylboronic Acids

DeBergh, J. Robb; Niljianskul, Nootaree; Buchwald, Stephen L.

doi:10.1021/ja405949a

Cited by 107 publications

(55 citation statements)

References 39 publications

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“…To address this limitation, a new protocol was developed by Buchwald and co-workers [24]. They demonstrated that phenyl chlorosulfate represents an excellent [SO 2 Cl] + synthon in the context of Pd catalyzed Suzuki Miyaura cross-coupling, which provided different kinds of sulfonamides in good to excellent yields.…”

Section: Synthesis Of Sulfonamidesmentioning

confidence: 99%

Sulfur Containing Scaffolds in Drugs: Synthesis and Application in Medicinal Chemistry

Feng¹,

Tang²,

Liang³

et al. 2016

CTMC

1,512

641

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The impact of the development of sulfur therapeutics is instrumental to the evolution of the pharmaceutical industry. Sulfur-derived functional groups can be found in a broad range of pharmaceuticals and natural products. For centuries, sulfur continues to maintain its status as the dominating heteroatom integrated into a set of 362 sulfur-containing FDA approved drugs (besides oxygen or nitrogen) through the present. Sulfonamides, thioethers, sulfones and Penicillin are the most common scaffolds in sulfur containing drugs, which are well studied both on synthesis and application during the past decades. In this review, these four moieties in pharmaceuticals and recent advances in the synthesis of the corresponding core scaffolds are presented.

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Section: Synthesis Of Sulfonamidesmentioning

confidence: 99%

Sulfur Containing Scaffolds in Drugs: Synthesis and Application in Medicinal Chemistry

Feng¹,

Tang²,

Liang³

et al. 2016

CTMC

1,512

641

View full text Add to dashboard Cite

show abstract

“…Der markante Unterschied zwischen [Cu(dap) 2 ]Cl und Ruthenium‐, Iridium‐ oder Eosin‐Y‐Katalysatoren deutet auf eine für den hier berichteten Gesamtprozess essentielle Rolle des Kupfers hin. Vermutlich wird SO 2 Cl16, 17 koordiniert und stellt es so als reaktives Intermediat zur Verfügung. Die Quantenausbeute dieses Prozesses wurde mit 12 % bestimmt, was einen Radikalkettenmechanismus ausschließt.…”

Section: Methodsunclassified

Trifluormethylchlorsulfonylierung von Alkenen – Hinweise auf einen Innensphärenmechanismus eines Kupferphenanthrolin‐Photoredoxkatalysators

et al. 2015

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Die Trifluormethylchlorsulfonierung von Alkenen gelingt durch die Kombination von sichtbarem Licht und [Cu(dap)2]Cl als Photoredoxkatalysator. Im Gegensatz dazu katalysieren [Ru(bpy)3]Cl2, [Ir(ppy)2(dtbbpy)]PF6 oder Eosin Y eine Trifluormethylchlorierung. [Cu(dap)2]Cl spielt in diesem Prozess eine zweifache Rolle: Einerseits agiert es als Elektronentransferreagens, andererseits koordiniert es die Reagentien für die Bindungsbildung.

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“…41 A wide range of organometallics were successfully utilized. Simply substituted aryl Grignards added rapidly with only one equivalent of nucleophile (entries [13][14][15][16][17][18], while more hindered o-substituted nucleophiles typically required longer reaction times and additional equivalents of nucleophile for full consumption of the inner salt (entries [19][20][21]. The addition of Lewis acids in an [27][28].…”

Section: Scheme 1 Precedent (7) and Proposed (8) Reaction Of C-nuclementioning

confidence: 99%

The Synthesis of Alkyl and (Hetero)aryl Sulfonamides From Sulfamoyl Inner Salts

et al. 2015

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An approach to the synthesis of sulfonamides from sulfamoyl inner salts and organometallic species is presented. A range of sulfamoyl carbamates, amines, and metals are explored. Primary, secondary, and tertiary alkyl-, aryl-, and heteroaryllitihium and magnesium nucleophiles were successful. This approach yields bench-stable intermediates and avoids many of the functional group incompatibilities, regioselectivity issues, and high-energy reagents generally associated with the synthesis of sulfonamides. Additionally, the products may be purified by basic extraction or salt formation, avoiding chromatography.

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Synthesis of Aryl Sulfonamides via Palladium-Catalyzed Chlorosulfonylation of Arylboronic Acids

Abstract: A palladium-catalyzed method for the preparation of sulfonamides is described. The process exhibits significant functional group tolerance and allows for the preparation of a number of arylsulfonyl chlorides and sulfonamides under mild conditions.

Cited by 107 publications

References 39 publications

Sulfur Containing Scaffolds in Drugs: Synthesis and Application in Medicinal Chemistry

Sulfur Containing Scaffolds in Drugs: Synthesis and Application in Medicinal Chemistry

Trifluormethylchlorsulfonylierung von Alkenen – Hinweise auf einen Innensphärenmechanismus eines Kupferphenanthrolin‐Photoredoxkatalysators

The Synthesis of Alkyl and (Hetero)aryl Sulfonamides From Sulfamoyl Inner Salts

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