- C-H borylation by platinum catalysis
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Herein, we describe the platinum-catalyzed borylation of aromatic C-H bonds. N-Heterocyclic carbene-ligated platinum catalysts are found to be efficient catalysts for the borylation of aromatic C(sp2)-H bonds when bis(pinacolato)diboron is used as the boron source. The most remarkable feature of these Pt catalysts is their lack of sensitivity towards the degree of steric hindrance around the C-H bonds undergoing the borylation reaction. These Pt catalysts allow for the synthesis of sterically congested 2,6-disubstituted phenylboronic esters, which are otherwise difficult to synthesize using existing C-H borylation methods. Furthermore, platinum catalysis allows for the site-selective borylation of the C-H bonds ortho to fluorine substituents in fluoroarene systems. Preliminary mechanistic studies and work towards the synthetic application of this platinum catalyzed C-H borylation process are described.
- Furukawa, Takayuki,Tobisu, Mamoru,Chatani, Naoto
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supporting information
p. 332 - 342
(2017/05/09)
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- User-Friendly Platinum Catalysts for the Highly Stereoselective Hydrosilylation of Alkynes and Alkenes
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With a view to addressing the shortcomings of traditional catalysts, a new generation of outstanding N- heterocyclic carbene platinum(0) complexes for the hydrosilylation of unsaturated carbon-carbon bonds is reported. Their discovery and application to the stereoselective addition of various silanes to silylated alkynes, terminal acetylenes, and olefins is presented. Insights into the catalytic cycle and the origin of the stereoselectivity are also discussed.
- Dierick, Steve,Vercruysse, Emilie,Berthon-Gelloz, Guillaume,Mark?, István E.
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supporting information
p. 17073 - 17078
(2015/11/16)
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- C-H Functionalization at Sterically Congested Positions by the Platinum-Catalyzed Borylation of Arenes
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Despite significant progress in the area of C-H bond functionalization of arenes, no general method has been reported for the functionalization of C-H bonds at the sterically encumbered positions of simple arenes, such as mesitylene. Herein, we report the development of the first platinum-based catalyst for C-H borylation of arenes and heteroarenes. Notably, this method exhibited high tolerance toward steric hindrance and provided rapid access to a series of 2,6-disubstituted phenylboronic esters, valuable building blocks for further elaborations.
- Furukawa, Takayuki,Tobisu, Mamoru,Chatani, Naoto
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supporting information
p. 12211 - 12214
(2015/10/12)
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- Copper-catalyzed cross-coupling of vinylsiloxanes with bromoalkynes: Synthesis of enynes
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Enynes are versatile building blocks in organic synthesis. A copper-catalyzed Hiyama-type cross-coupling of vinylsiloxanes with bromoalkynes is presented. This mild and efficient method led to the formation of various sensitive enynes. The use of cis, trans, and 1,1′-disubstituted vinylsiloxanes was allowed, and full retention of stereochemistry was observed. Sensitive groups such as halides, unsaturated ketones, and aldehydes were fully tolerated.
- Cornelissen, Loic,Lefrancq, Maxime,Riant, Olivier
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supporting information
p. 3024 - 3027
(2014/06/23)
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- Copper-catalyzed Hiyama cross-coupling using vinylsilanes and benzylic electrophiles
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Allylbenzene derivatives are ubiquitous frameworks in organic chemistry. Herein is described an efficient copper-catalyzed cross-coupling reaction using vinylsilanes and benzyl bromides, leading to the synthesis of allylbenzenes. This methodology allows the use of cis, trans and 1,1′-disubstituted vinylsilanes as well as a large number of sensitive moieties. the Partner Organisations 2014.
- Cornelissen,Cirriez,Vercruysse,Riant
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supporting information
p. 8018 - 8020
(2014/07/08)
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