Organic & Biomolecular Chemistry
Paper
Notes and references
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Fig. 3 X-ray structure of palladium(II) complex 10.
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reduced to 0.1 mol%. These first results demonstrate that
complex 10 derived from triazolylphosphine 2f is a highly
active catalyst in the Suzuki–Miyaura cross-coupling reactions
of aryl chlorides.
Conclusion
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We developed an efficient synthesis of 1,2,3-triazolyl-4-phos-
phines from silyl alkynylphosphine-boranes, relying on a
tandem desilylation with TBAF/Click transformation and sub-
sequent decomplexation by treatment with DABCO. The pro-
cedure is general, being readily applicable to diaryl-, dialkyl-
and alkyl-aryl-P derivatives and to benzyl- and aryl-azides. The
presence of sensitive functional groups such as a halide or an
acetyl group is tolerated in contrast to previously reported tri-
azolylphosphine syntheses, which involved the use of metallic
bases. Various original functional groups such as a sugar, a
sulfanyl moiety or a paracyclophane could also be introduced.
Moreover the first example of an enantioenriched P-stereo-
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through the reported methodology. Our preliminary studies on
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synthesized triazolylphosphines and notably from the chiral
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Acknowledgements
This work was supported by CNRS, Crunch (interregional
organic chemistry network), the Région Basse-Normandie, the 13 (a) H. Staudinger and J. Meyer, Helv. Chim. Acta, 1919, 2,
European Union (ISCE-Chem & INTERREG IVa program) and
Labex Synorg. COST ACTION CM0802 “PHOSCINET” is also
635–646; (b) E. Saxon and C. R. Bertozzi, Science, 2000, 287,
2007–2010.
acknowledged for support. R.V. and E.B. respectively acknowl- 14 (a) J. S. Harvey, G. T. Giuffredi and V. Gouverneur, Org.
edge the Ministère de la Recherche and the Région Basse-
Normandie for graduate fellowships.
Lett., 2010, 12, 1236–1239; (b) E. A. Slutsky Smith,
G. Molev, M. Botoshansky and M. Gandelman, Chem.
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