Cyclododecene isomeric separation by (supported) rhodium(i)-catalysed selective dehydrogenative borylation reaction

Cyclododecene, commercially available as a cis/trans mixture, reacts with dipinacolborane (BPin) only through the cis isomer, during the Rh(i)-XantPhos-catalyzed dehydrogenative monoborylation reaction, leaving the starting trans-cyclododecene untouched. In this way, both diastereoisomers can now be...

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Detalhes bibliográficos
Autores: Singh, Amravati S., Leyva, Antonio
Formato: artículo
Estado:Versión publicada
Fecha de publicación:2023
País:España
Recursos:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/357243
Acesso em linha:http://hdl.handle.net/10261/357243
Access Level:acceso abierto
Descrição
Resumo:Cyclododecene, commercially available as a cis/trans mixture, reacts with dipinacolborane (BPin) only through the cis isomer, during the Rh(i)-XantPhos-catalyzed dehydrogenative monoborylation reaction, leaving the starting trans-cyclododecene untouched. In this way, both diastereoisomers can now be easily separated. The catalytic Rh(i)-phosphine complex progressively degrades under the reaction conditions; thus we also present here a cheap, ligandless Rh(i)-supported zeolite NaY catalyst, equally selective for the dehydrogenative monoborylation reaction. These results provide a new methodology for macrocyclic alkene diastereoisomeric separation.