Coupling reactions on bicyclo[1.1.1]pentane cage bridgeheads
| Authors | |
|---|---|
| Year of publication | 2003 |
| Type | Article in Proceedings |
| Conference | YoungChem 2003, Book of Abstracts |
| MU Faculty or unit | |
| Citation | |
| Web | http://yc2003.ch.pw.edu.pl/ |
| Field | Organic chemistry |
| Keywords | Cross-coupling; bicyclopentanes; transition metal catalyzed reaction |
| Description | Experimental effort disclosing the possibility of transition-metal mediated cross-coupling reactions on electrophilic bicyclo[1.1.1]pentane cage bridgeheads is described. It has been shown that the bridgehead-halogen bond in bicyclo[1.1.1]pentanes can undergo oxidative addition towards low-valent nickel species, yielding a new complex which reacts with organomagnesium or organolithium reagents to form a new C-C bond. Thus, the unsymmetrically substituted bicyclo[1.1.1]pentane derivatives posessing, for example, aryl funcional moieties on the bridgeheads could be prepared. Likewise, the protocol could be applied to the synthesis of [1.1.1]propellane oligomers ([n]staffanes), a class of compounds exploitable as the building blocks for supramolecular chemistry and molecular electronics |
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