Journal
ORGANIC LETTERS
Volume 19, Issue 24, Pages 6586-6589Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b03294
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Funding
- DFG
- China Scholarship Council
- Swedish Research Council
- Knut and Alice Wallenberg Foundation
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An efficient methodology for the synthesis of vinyl-, allyl-, and (E)-2-boryl allylboronates from propargylic alcohols via Cu-catalyzed borylation under mild conditions is reported. In the presence of commercially available Cu(OAc)(2) or Cu(acac)(2) and Xantphos, the reaction affords the desired products in up to 92% yield with a broad substrate scope (43 examples). Isolation of an allenyl boronate as the reaction intermediate suggests that an insertion elimination-type reaction, followed by borylcupration, is involved in the borylation of propargylic alcohols.
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