Direct Propargylation of ortho-Quinone Methides with Alkynyl Zinc Reagents: An Application to the One-Pot Synthesis of 2,3-Disubstituted Benzofurans

A transition-metal-free propargylation of ortho-quinone methides (o-QMs) with alkynyl zinc reagents was achieved. A conjugate alkynylation of an o-QM and subsequent cyclization sequence in the presence of KOt-Bu for the synthesis of 2,3-disubstituted benzofurans in one pot was developed. This effici...

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Bibliographic Details
Published inSynlett Vol. 31; no. 8; pp. 818 - 822
Main Authors Sun, Manman, Song, Jinyu, Wang, Lei, Yin, Wenguang, Miao, Maozhong, Ren, Hongjun
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 28.05.2020
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SYSTEM
ENANTIOSELECTIVE SYNTHESIS
ANNULATION
alkynyl zinc reagents
benzofurans
ALLYLIC ALKYLATION
propargylation
TERMINAL ALKYNES
INDOLES
NUCLEOPHILES
ortho-quinone methides
CATALYZED 1,4-ADDITION
CYCLIZATION
CONJUGATE ADDITION
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Summary:A transition-metal-free propargylation of ortho-quinone methides (o-QMs) with alkynyl zinc reagents was achieved. A conjugate alkynylation of an o-QM and subsequent cyclization sequence in the presence of KOt-Bu for the synthesis of 2,3-disubstituted benzofurans in one pot was developed. This efficient strategy exhibits good functional-group compatibility and gives moderate to good yields. The present reaction might serve as an attractive method for the synthesis of polysubstituted benzofurans.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0039-1691739