122nd General Meeting of the KCS

Type Poster Presentation
Area Organic Chemistry
Room No. Grand Ballroom
Time 10월 18일 (목요일) 11:00~12:30
Code ORGN.P-61
Subject Ligand-Controlled Copper-Catalyzed Regioselective Hydroborylation and Borylstannylation of Allensulfonamides
Authors Haeeun Lee, Jin Kyoon Park*
Department of Chemistry, Pusan National University, Korea
Abstract

Bimetallic alkenes have been proven to be versatile compounds for the formation of multi-functionalized valuable compounds through carbon-carbon and carbon-hetero atom bond formations by wisely choosing the coupling partners. Therefore, the transformation of bimetallic species that allow the introduction of diverse functionalities will be a highly demandable owing to the differential reactivities associated with them. In a careful consideration of these features and continuation of our recent research on temporary coordination of a neighboring sulfone group to a metal for stereoselectivity control, herein, we are presenting the results of a highly regio- and stereoselective copper-catalyzed hydroborylation of allensulfonamide with bis(pinacolato)diboron. The subsequent trapping of the intermediate by tri-n-butyltinmethoxide allowed a three-component coupling with same reactivity. Because of the equilibrium associated with this type of functionalized stannane alkenes, however, we observed the formation of only linear β-borylated allyltin under the same reaction condition. We also demonstrated the diverse transformations using these bimetallics compound to many interesting compounds. Reference 1.S. B. Thorpe, X. Guo,W. L. Stantos, Chem. Commun. 2011, 47, 424; b) B. Jung, A. H. Hoveyda, J. Am. Chem. Soc. 2012, 134, 1490 2.W. Yuan, S. Ma, Adv. Synth. Catal. 2012, 354, 1867; d) F. Meng, B. Jung, F. Haeffner, A. H. Hoveyda, Org. Lett. 2013, 15, 1414 3.Yuki akemoto, Hiroto Yoshida, Ken Takaki, Synthesis 2014, 46, 3024–3032

E-mail helee6161@gmail.com