Issue 4, 2024

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

Abstract

Cyclododecene, commercially available as a cis/trans mixture, reacts with dipinacolborane (BPin)2 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.

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

Supplementary files

Article information

Article type
Research Article
Submitted
27 Oct 2023
Accepted
17 Dec 2023
First published
18 Dec 2023
This article is Open Access
Creative Commons BY-NC license

Org. Chem. Front., 2024,11, 1124-1131

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

A. S. Singh and A. Leyva-Pérez, Org. Chem. Front., 2024, 11, 1124 DOI: 10.1039/D3QO01786A

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