1147765-35-2Relevant academic research and scientific papers
Copper(I)-catalyzed highly regio- and stereoselective hydrosilylation of terminal alkynes with boryldisiloxane
Zhou, Hui,Wang, Yan-Bo
, p. 2512 - 2516 (2015/04/14)
By employing 1,1,3,3-tetramethyl-1,3-(pinacolboryl)disiloxane as a novel silicon source, the N-heterocyclic carbene copper complex catalyzed hydrosilylation of terminal alkynes was developed to prepare vinyldisiloxanes in a highly regio- and stereoselective manner. A number of functional groups, including ether, ester, cyano, nitro, halo, hydroxyl, cyclopropyl, and aryl groups, were tolerated under the optimized conditions. A mechanistic investigation was undertaken by using density functional theory calculations. This approach allows facile entry to unsymmetrical disubstituted (E)-alkenes by Pd-catalyzed cross-coupling reactions.
Preparation of vinyl silyl ethers and disiloxanes via the silyl-heck reaction of silyl ditriflates
Martin, Sara E. S.,Watson, Donald A.
supporting information, p. 13330 - 13333 (2013/09/24)
Vinyl silyl ethers and disiloxanes can now be prepared from aryl-substituted alkenes and related substrates using a silyl-Heck reaction. The reaction employs a commercially available catalyst system and mild conditions. This work represents a highly practical means of accessing diverse classes of vinyl silyl ether substrates in an efficient and direct manner with complete regiomeric and geometric selectivity.
Palladium-catalysed cross-coupling of vinyldisiloxanes with benzylic and allylic halides and sulfonates
Frye, Elizabeth C.,O'Connor, Cornelius J.,Twigg, David G.,Elbert, Bryony,Laraia, Luca,Hulcoop, David G.,Venkitaraman, Ashok R.,Spring, David R.
supporting information; experimental part, p. 8774 - 8779 (2012/09/21)
The Hiyama cross-coupling reaction is a powerful method for carbon-carbon bond formation. To date, the substrate scope of this reaction has predominantly been limited to sp2-sp2 coupling reactions. Herein, the palladium-catalysed Hiyama type cross-coupling of vinyldisiloxanes with benzylic and allylic bromides, chlorides, tosylates and mesylates is reported. A wide variety of functional groups were tolerated, and the synthetic utility of the methodology was exemplified through the efficient total synthesis of the cytotoxic natural product bussealin A. In addition, the antiproliferative ability of bussealin A was evaluated in two cancer-cell lines. Copyright
Vinyldisiloxanes: Their synthesis, cross coupling and applications
Sore, Hannah F.,Boehner, Christine M.,Laraia, Luca,Logoteta, Patrizia,Prestinari, Cora,Scott, Matthew,Williams, Katharine,Galloway, Warren R. J. D.,Spring, David R.
experimental part, p. 504 - 515 (2011/03/17)
During the studies towards the development of pentafluorophenyldimethylsilanes as a novel organosilicon cross coupling reagent it was revealed that the active silanolate and the corresponding disiloxane formed rapidly under basic conditions. The discovery that disiloxanes are in equilibrium with the silanolate led to the use of disiloxanes as cross coupling partners under fluoride free conditions. Our previous report focused on the synthesis and base induced cross coupling of aryl substituted vinyldisiloxanes with aryl halides; good yields and selectivities were achieved. As a continuation of our research, studies into the factors which influence the successful outcome of the cross coupling reaction with both alkyl and aryl substituted vinyldisiloxanes were examined and a proposed mechanism discussed. Further investigation into expanding the breadth and diversity of substituted vinyldisiloxanes in cross coupling was explored and applied to the synthesis of unsymmetrical trans-stilbenes and cyclic structures containing the trans-alkene architecture.
Fluoride-free cross coupling using vinyldisiloxanes
Sore, Hannah F.,Boehner, Christine M.,MacDonald, Simon J. F.,Norton, David,Fox, David J.,Spring, David R.
supporting information; experimental part, p. 1068 - 1071 (2009/05/30)
Vinyldisiloxanes equilibrate with the corresponding silanolates under basic conditions and subsequently undergo palladium catalysed cross coupling with aryl/heteroaryl iodides and bromides. The Royal Society of Chemistry 2009.
