Journal
TETRAHEDRON
Volume 74, Issue 50, Pages 7228-7236Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2018.10.055
Keywords
Oxidative cross-coupling; Palladium catalysis; Allyl(trimethyl)silane; Aryl boronic acid
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Funding
- National Natural Science Foundation of China [21502006]
- Beijing Institute of Technology (BIT)
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The first oxidative cross-coupling of allylsilanes with aryl boronic acids has been developed by palladium catalysis. The reaction between beta-substituted allyl(trimethyl)silanes and a wide range of aryl boronic acids afforded allylarenes in moderate to good yields and excellent selectivity. On the basis of experimental results and literature reports, it was suggested that the reaction might start from transmetalation of aryl boronic acid with AgOAc followed by transmetalation with Pd(II) to give an arylpalladium acetate complex as a key intermediate. This intermediate underwent either electrophilic addition/desilylation or transmetalation with allylsilane and subsequent reductive elimination to give the final product. (C) 2018 Elsevier Ltd. All rights reserved.
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