Organic Chemistry: Current Research
Open Access

Controlling the regio- and stereoselectivity of hydrosilylation reaction catalyzed by platinum(0) complexes bearing bulky N-heterocyclic ligand

10^th European Organic Chemistry Congress

March 21-22, 2019 | Rome, Italy

Malgorzata Bolt, Patrycja Zak and Cezary Pietraszuk

Adam Mickiewicz University in Poznan, Poland

Posters & Accepted Abstracts: Organic Chem Curr Res

Abstract :

Hydrosilylation, which usually refers to addition of silanes to double or triple C-C bounds, is one of the most powerful synthetic methods of production organosilicon compounds (Figure 1). This reaction gives possibility for simple functionalization of many organic compounds and for synthesis wide spectrum of silanes derivatives. Although there are many different catalytic systems characterized by good activity, regio- and stereoselectivity still remains as a great problem of this process. The reaction can lead to a several different products and can also be accompanied by several side-processes like hydrogenation, isomerization, dehydrogenative silylation, olefin oligomerization or redistribution of silanes. The number of potential products increases when we use secondary silanes instead of tertiary, because of the possibility of bis-hydrosilylation. The situation gets also more complicated when we use substrates containing more functionalities which can react, for example enynes, dienes or diynes. Presented research deals with the problem of selectivity of the hydrosilylation reaction. Using platinum (0) complex bearing bulky N-heterocyclic carbene ligand and by careful tuning of the reaction conditions such as temperature and substrates ratio, we were able to control course of the reaction and obtain desired products with good yields and selectivity. The research concern hydrosilylation of terminal acetylenes with disubstituted silanes as well as hydrosilylation of dienes, diynes and enynes with trisubstituted silanes.

ACKNOWLEDGMENT: The research was financed by the National Science Center (Poland) under the SONATA Project No. UMO-2016/23/D/ST5/00417.

Recent Publications

1. Zak P, Bolt M, Kubicki M, Pietraszuk C (2018) Highly selective hydrosilylation of olefins and acetylenes by platinum(0) complexes bearing bulky N-heterocyclic carbene ligands. Dalton Trans. 47:1903-1910

2. Zak P, Bolt M, Pietraszuk C (2018) Selective synthesis of E-vinylsilanes and E,E-divinylsilanes via platinumcatalyzed hydrosilylation of alkynes with secondary silanes. RSC Adv. 8:40016-40021

3. Mo Z, Xiao J, Deng L (2014) Regio- and Stereoselective Hydrosilylation of Alkynes Catalyzed by Three- Coordinate Cobalt(I) Alkyl and Silyl Complexes. J. Am. Chem. Soc 136:17414–17417

4. Sang H L, Yu S, Ge S (2018) Cobalt-catalyzed regioselective stereoconvergent Markovnikov 1,2-hydrosilylation of conjugated dienes. Chem. Sci. 9:973-978.

5. Raya B, Jing S, Balasanthiran V, RajanBabu T V, (2017) Control of Selectivity through Synergy between Catalysts, Silanes, and Reaction Conditions in Cobalt-Catalyzed Hydrosilylation of Dienes and Terminal Alkenes. ACS Catal. 7:2275-2283

Biography :

MaÃ?Â?gorzata BoÃ?Â?t is a graduate student in Adam Mickiewicz University in Poznan and she is preparing her master thesis in the Department of Organometallic Chemistry in the Faculty of Chemistry. Her current research interests focuses on synthesis of transition metal catalysts and use obtained compounds in catalytic systems such as hydrosilylation and terminal acetylenes dimerization. Her current research concerns mainly on platinum(0) catalysts bearing bulky N-heterocyclic carbene ligands. Steric hindrance around metal center caused by the presence of the bulky ligand have a great influence on activity and selectivity in the studied reactions.