Journal
JOURNAL OF ORGANOMETALLIC CHEMISTRY
Volume 693, Issue 15, Pages 2637-2640Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jorganchem.2008.05.006
Keywords
boron; porphyrin; cross-metathesis; Ru-catalyst
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Porphyrins with (un)saturated side-chains containing boron residues were developed as synthons for porphyrin functionalisation. Porphyrins with mono and bis-substituted unsaturated boronyl residues were prepared in good yields (52-66%) using a cross-metathesis approach in the presence of Grubbs I-generation catalysts. In all cases complete E-stereoselectivity (100%) was observed. Furthermore, formal cross-metathesis products with alpha,beta-unsaturated chains smoothly underwent addition with bis(pinacolato) diboron [(Me(4)C(2)O(2))B-B(O(2)C(2)Me(4))] to yield the corresponding saturated boron compounds in 60-70% yields. (C) 2008 Elsevier B.V. All rights reserved.
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