Vinylation of aromatic halides using inexpensive organosilicon reagents. Illustration of design of experiment protocols

SE Denmark, CR Butler

Index: Denmark, Scott E.; Butler, Christopher R. Journal of the American Chemical Society, 2008 , vol. 130, # 11 p. 3690 - 3704

Full Text: HTML

Citation Number: 72

Abstract

The preparation of styrenes by palladium-catalyzed cross-coupling of aromatic iodides and bromides with divinyltetramethyldisiloxane (DVDS) in the presence of inexpensive silanolate activators has been developed. To facilitate the discovery of optimal reaction conditions, Design of Experiment (DoE) protocols were used. By the guided selection of reagents, stoichiometries, temperatures, and solvents, the vinylation reaction was rapidly optimized ...

~99%

~67%

~53%

~79%

~71%

~61%

~81%

~79%

~90%

~80%

~48%

~82%

~91%

~67%

~53%

Copper-carbene complexes as catalysts in the synthesis of fu...

[Lebel, Helene; Davi, Michael; Diez-Gonzalez, Silvia; Nolan, Steven P. Journal of Organic Chemistry, 2007 , vol. 72, # 1 p. 144 - 149]

Palladium/imidazolium salt catalyzed coupling of aryl halide...

[Grasa, Gabriela A.; Nolan, Steven P. Organic Letters, 2001 , vol. 3, # 1 p. 119 - 120]

A Predictably Selective Nitration of Olefin with Fe (NO3) 3 ...

[Maity, Soham; Manna, Srimanta; Rana, Sujoy; Naveen, Togati; Mallick, Arijit; Maiti, Debabrata Journal of the American Chemical Society, 2013 , vol. 135, # 9 p. 3355 - 3358]

Competitive Elimination-Substitution Reactions. Some Dramati...

[Journal of the American Chemical Society, , vol. 86, p. 3072 - 3075]

Vinylation of aryl bromides using an inexpensive vinylpolysi...

[Organic Letters, , vol. 8, # 1 p. 63 - 66]