Palladium-catalyzed coupling of vinyl triflates with organostannanes.  Synthetic and mechanistic studies

Scott, William J.; Stille, J. K.

doi:10.1021/ja00271a037

Cited by 482 publications

(210 citation statements)

References 4 publications

Supporting

Mentioning

198

Contrasting

Unclassified

Order By: Relevance

“…For the coupling of organostannanes with vinyl [210] and aryl triflates, [211,212] LiCl has been used as an additive. Iodide salts have also been shown to promote other coupling reactions with aryl triflates.…”

Section: The Open Associative Transmetalationmentioning

confidence: 99%

The Mechanisms of the Stille Reaction

2004

View full text Add to dashboard Cite

Eighteen years ago in Angewandte Chemie John K. Stille reviewed a novel methodology, which eventually became known by his name, for the coupling of organostannanes with organic electrophiles. Since then that seed has blossomed into a multifaceted methodology full of hidden possibilities to explore, discover, and enjoy. Very recent modifications are making synthetic wishes come true that were only dreamed of a few years ago. Moreover, as important advances are being made in the understanding of the mechanistic details of the process, it is becoming increasingly possible to apply this essential reaction and its new variants in a less empirical way. The purpose of this Review is to give a critical account of this progress.

show abstract

Section: The Open Associative Transmetalationmentioning

confidence: 99%

The Mechanisms of the Stille Reaction

2004

View full text Add to dashboard Cite

show abstract

“…1 und 2). [33,34] Zugabe von KF oder CsF (Nr. 3 und 4) resultierte wiederum in vorwiegender C-OTf-Inserierung.…”

unclassified

Mediumeffekte in Palladium‐katalysierten Kreuzkupplungen und Implikationen bezüglich der katalytisch aktiven Spezies

Proutière

Schoenebeck

2011

Angewandte Chemie

View full text Add to dashboard Cite

“…Thus, (±)-7a was synthesized according to the directives given by Snyder et al 15 in the synthesis of abietanoid o-quinones, except that the Stang's protocol 16 (triflic anhydride instead of N-phenyltriflimide 17 /LDA system) was applied to obtain monoenoltriflate 11a (60% yield). As supposed, a palladium-catalysed reaction (Stille cross coupling 18 ) performed with 11a and the vinylstannane 19 built-up the diene moiety of 7b in good yield (85%).…”

Section: Resultsmentioning

confidence: 85%

Synthesis of rearranged unsaturated drimane derivatives

Miranda¹,

Conceição²,

Zukerman-Schpector³

et al. 2001

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

O presente trabalho relata a preparação e aplicação de três vinilcicloexenos devidamente funcionalizados (2,2-dimetil-3-vinilcicloex-3-en-1-ol, 2,2-dimetil-3-vinilcicloex-3-en-1-ona e 3,3-dimetil-2-vinilcicloexeno) em reações de Diels-Alder com ésteres a,b-insaturados (tiglato de metila e angelato de metila). Esta abordagem levou à síntese racêmica de dez octalinas possuindo esqueleto drimânico rearranjado (4 diastereoisômeros do 1-metoxicarbonil-6-hidroxi-1,2,5,5-tetrametil-1, 2,3,5,6,7,8,8a-octaidronaftaleno; 1-metoxicarbonil-6-oxo-1,2,5,5-tetrametil-1,2,3,4,5,6,7,8-ocataidronaftaleno; 2-metoxicarbonil-6-oxo-1,2,5,5-tetrametil-1,2,3,5,6,7, 8,8a-octaidronaftaleno; 3 diastereoisômeros do 1-metoxicarbonil-1,2,5,5-tetrametil-1,2,3,5,6,7,8,8a-octaidronaftaleno e 2-metoxicarbonil-1,2,5,5-tetrametil-1,2, 3,5,6,7,8,8a-octaidronaftaleno). Para a preparação dos dienos, utilizou-se a reação de acoplamento catalisada por paládio (reação de Stille) entre enoltriflatos (preparados pelo protocolo de Stang) e tri-n-butilvinilestanana. A estereoquímica relativa dos produtos foi estabelecida a partir de métodos espectroscópicos e análise de difração de raios-X de alguns dos derivados. Estes dados podem servir para a identificação de novos produtos naturais e corrigir algumas estruturas da literatura.A full account to the preparation and application of three appropriately substituted vinylcyclohexenes (2,2-dimethyl-3-vinylcyclohex-3-en-1-ol, 2,2-dimethyl-3-vinylcyclohex-3-en-1-one and 3,3-dimethyl-2-vinylcyclohexene) in thermal Diels-Alder reactions with a,b-unsaturated esters (methyl tiglate and methyl angelate) is given. This approach delivered the racemic synthesis of ten octalin derivatives bearing a rearranged drimane skeleton (4 diastereomers of 1-methoxycarbonyl-6-hydroxy-1, 2,5,5-tetramethyl-1,2,3,5,6,7, 8,8a-octahydronaphthalene; 1-methoxycarbonyl-6-oxo-1,2,5,5-tetramethyl-1,2,3,4,5,6,7,8-octahydronaphthalene; 2-methoxycarbonyl-6-oxo-1,2,5,5-tetramethyl-1,2,3,5,6,7,8,8a-octahydronaphthalene; 3 diastereomers of 1-methoxycarbonyl-1,2,5,5-tetramethyl-1,2,3,5,6,7,8,8a-octahydronaphthalene and 2-methoxycarbonyl-1,2,5,5-tetramethyl-1,2,3,5,6,7,8,8a-octahydronaphthalene). Central synthetic features included preparation of enoltriflates by Stang's protocol and the successful palladium-catalyzed cross-coupling reaction (Stille reaction) of the triflate with the tri-nbutylvinylstannane. The octalins relative stereochemistry was unequivocally ascertained by spectroscopic methods and/or X-ray crystallography and these data now stand as useful tools to support the correct assignment of related natural products usually isolated in minute amounts.

show abstract

Palladium-catalyzed coupling of vinyl triflates with organostannanes. Synthetic and mechanistic studies

Cited by 482 publications

References 4 publications

The Mechanisms of the Stille Reaction

The Mechanisms of the Stille Reaction

Mediumeffekte in Palladium‐katalysierten Kreuzkupplungen und Implikationen bezüglich der katalytisch aktiven Spezies

Synthesis of rearranged unsaturated drimane derivatives

Contact Info

Product

Resources

About