Palladium-catalyzed coupling of aryl arenesulfonates with organostannanes

Badone, Domenico; Cecchi, Roberto; Guzzi, U.

doi:10.1021/jo00049a047

Cited by 65 publications

(8 citation statements)

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“…Herein, we show that the para ‐nitrophenylsulfonate (nosyl; Ns) group offers the required properties and that nosylates can act as excellent partners in various Pd‐catalyzed cross‐coupling reactions (Scheme ). To the best of our knowledge, the reactivity of various vinyl nosylates with palladium catalysts in cross‐coupling reactions has not been reported so far, the case of aryl nosylates being discussed only once in a Stille coupling reaction 13. Recently, the Skrydstrup group employed an aryl nosylate in a Heck reaction catalyzed by a nickel complex;14 however, only one example was reported and the product was isolated in low yield (17 %).…”

Section: Methodsmentioning

confidence: 99%

“…To the best of our knowledge, the reactivity of various vinyl nosylates with palladium catalysts in cross-coupling reactions has not been reported so far, the case of aryl nosylates being discussed only once in a Stille coupling reaction. [13] Recently, the Skrydstrup group em-ployed an aryl nosylate in a Heck reaction catalyzed by a nickel complex; [14] however, only one example was reported and the product was isolated in low yield (17 %).…”

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confidence: 99%

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Vinyl Nosylates: An Ideal Partner for Palladium‐Catalyzed Cross‐Coupling Reactions

Cheval¹,

Dikova²,

Blanc³

et al. 2013

Chemistry A European J

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In a hurry to leave! Nosylates act as an excellent leaving group in various palladium‐catalyzed cross‐couplings, such as Suzuki, Stille, Heck, and Sonogashira reactions (see scheme). Crystalline, stable, and cheap vinyl and aryl nosylates proved better than classical halides and triflates, consistently giving higher yields of coupling products. Their usefulness in CC bond formation was also demonstrated by the rapid synthesis of the alkaloid dubamine.

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Section: Methodsmentioning

confidence: 99%

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confidence: 99%

Vinyl Nosylates: An Ideal Partner for Palladium‐Catalyzed Cross‐Coupling Reactions

Cheval¹,

Dikova²,

Blanc³

et al. 2013

Chemistry A European J

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“…27 The reaction has been extended to the less expensive aryl fluorosulfonates 28 and aryl arenesulfonates. 29 These reactions proceed in good yield unless the aryl ring contains electrondonating substituents. Allylation of Imines.…”

Section: Ohmentioning

confidence: 99%

Allyltributylstannane

Castellino

Volk

Patil

et al. 2006

Encyclopedia of Reagents for Organic Synthesis

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“…However, the palladium-catalyzed coupling of aryl tosylates is rare. Only one paper has contained palladium-catalyzed coupling with arene sulfonates, and this work involved an electron-deficient aryl fluoroarene sulfonate [151]. One report of the carbonylation of an activated aryl tosylate has appeared [152].…”

Section: Use Of Sterically Hindered Bis(phosphine) Ligandsmentioning

confidence: 99%

Palladium‐Catalyzed Amination of Aryl Halides and Sulfonates

Hartwig

2002

Modern Arene Chemistry

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The transition metal catalyzed synthesis of arylamines by the reaction of aryl halides or triflates with primary or secondary amines has become a valuable synthetic tool for many applications. This process forms monoalkyl or dialkyl anilines, mixed diarylamines or mixed triarylamines, as well as N-arylimines, carbamates, hydrazones, amides, and tosylamides. The mechanism of the process involves several new organometallic reactions. For example, the CaN bond is formed by reductive elimination of amine, and the metal amido complexes that undergo reductive elimination are formed in the catalytic cycle in some cases by NaH activation. Side products are formed by b-hydrogen elimination from amides, examples of which have recently been observed directly. An overview that covers the development of synthetic methods to form arylamines by this palladium-catalyzed chemistry is presented. In addition to the synthetic information, a description of the pertinent mechanistic data on the overall catalytic cycle, on each elementary reaction that comprises the catalytic cycle, and on competing side reactions is presented. The review covers manuscripts that appeared in press before June 1, 2001. This chapter is based on a review covering the literature up to September 1, 1999. However, roughly one-hundred papers on this topic have appeared since that time, requiring an updated review.

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Palladium-catalyzed coupling of aryl arenesulfonates with organostannanes

Cited by 65 publications

References 2 publications

Vinyl Nosylates: An Ideal Partner for Palladium‐Catalyzed Cross‐Coupling Reactions

Vinyl Nosylates: An Ideal Partner for Palladium‐Catalyzed Cross‐Coupling Reactions

Allyltributylstannane

Palladium‐Catalyzed Amination of Aryl Halides and Sulfonates

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