Stille cross-coupling reaction of polyfluorovinylstannanes

Shen, Yanchang; Wang, Guoping

doi:10.1016/j.jfluchem.2003.10.013

Cited by 8 publications

(2 citation statements)

References 28 publications

(31 reference statements)

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“…The reaction proceeds best in THF as solvent with Pd(PPh 3 ) 4 as catalyst (9% mmol), CuI as cocatalyst at refluxing temperature for 24 h. Similarly the palladium/copper (I) iodide catalyzed coupling reaction of (Z)-a-fluoro-b-trifluoromethylvinylstannanes 71 with acid chloride proceeded smoothly under the same condition producing substituted (E)-a-fluoro-b-trifluoromethyl-a,b-unsaturated ketones 77 in 68-87% yield stereospecifically (Scheme 29) [25].…”

Section: Stereospecific Synthesis Of Polyfluoro-alkenes and Ab-unsatmentioning

confidence: 97%

“…The cross coupling reaction of (Z)-a-fluoro-b-trifluoromethylvinylstannanes 71 with aryl iodides in the presence of palladium/copper (I) iodide gave substituted (E)-a-fluoro-b-trifluoromethylethenes 76 stereospecifically in yields ranging from 50% to 98% (Scheme 29) [25]. The reaction proceeds best in THF as solvent with Pd(PPh 3 ) 4 as catalyst (9% mmol), CuI as cocatalyst at refluxing temperature for 24 h. Similarly the palladium/copper (I) iodide catalyzed coupling reaction of (Z)-a-fluoro-b-trifluoromethylvinylstannanes 71 with acid chloride proceeded smoothly under the same condition producing substituted (E)-a-fluoro-b-trifluoromethyl-a,b-unsaturated ketones 77 in 68-87% yield stereospecifically (Scheme 29) [25].…”

Section: Stereospecific Synthesis Of Polyfluoro-alkenes and Ab-unsatmentioning

confidence: 99%

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Recent advances in fluorinated vinylstannanes and their synthetic utility

Shen¹

2006

Journal of Organometallic Chemistry

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Section: Stereospecific Synthesis Of Polyfluoro-alkenes and Ab-unsatmentioning

confidence: 97%

Section: Stereospecific Synthesis Of Polyfluoro-alkenes and Ab-unsatmentioning

confidence: 99%

Recent advances in fluorinated vinylstannanes and their synthetic utility

Shen¹

2006

Journal of Organometallic Chemistry

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Stille Coupling

2010

Comprehensive Organic Name Reactions and Reagents

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The palladium‐catalyzed cross‐coupling reaction between an organostannane and an organic halide or its equivalent (e.g., acetate, triflate, and boronate) without a sp 3 ‐hybridized β‐hydrogen is generally known as the Stille coupling. It has been reported that the presence of a β‐(2‐pyridyl) group may change the migratory aptitude, owing to the chelation of the pyridyl group with tin or palladium. In addition, the Stille coupling often requires a phosphorus ligand and copper(I) iodide. Another series of catalysts consisting of palladium and phosphinous acid for the Stille coupling in aqueous solution without an organic co‐solvent have been developed recently. In particular, the recently developed proazaphosphatranes in the form of P(RNCH 2 CH 2 ) 3 N (R = benzyl, iso ‐butyl) facilitate the coupling of a variety of aryl chlorides with organotin compounds, with the compatibility for functional groups. Moreover, the Stille coupling can also be used for the preparation of carbonyl compounds in the presence of carbon monoxide or through the direct reaction with acyl halides, a reaction known as the carbonylative Stille cross‐coupling. However, this reaction also holds some intrinsic drawbacks so that it is gradually replaced by other coupling reactions. This reaction has very broad application in organic synthesis.

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Polyfunctional Tin Organometallics for Organic Synthesis

Fouquet¹,

Herve²

2005

Handbook of Functionalized Organometallics

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Stille cross-coupling reaction of polyfluorovinylstannanes

Cited by 8 publications

References 28 publications

Recent advances in fluorinated vinylstannanes and their synthetic utility

Recent advances in fluorinated vinylstannanes and their synthetic utility

Stille Coupling

Polyfunctional Tin Organometallics for Organic Synthesis

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