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钯(II)催化炔烃与含原酸酯的苯基硼酸的环化反应。

Palladium(II)-catalyzed annulation of alkynes with ortho-ester-containing phenylboronic acids.

作者信息

Tsukamoto Hirokazu, Kondo Yoshinori

机构信息

Graduate School of Pharmaceutical Sciences, Tohoku University, Aramaki-aza aoba 6-3, Aoba-ku, Sendai 980-8578, Japan.

出版信息

Org Lett. 2007 Oct 11;9(21):4227-30. doi: 10.1021/ol701776m. Epub 2007 Sep 15.

DOI:10.1021/ol701776m
PMID:17867697
Abstract

Palladium(II) catalyzes annulation of internal alkynes with methyl 2-boronobenzoate and (2-boronophenyl)acetate to provide 2,3-disubstituted indenones and 3,4-disubstituted 2-naphthols, respectively. The annulation reaction would proceed through transmetalation of Pd(II) with the boron reagents and insertion of the alkynes, followed by unprecedented 1,2-addition of the generated alkenylpalladium(II) species to the intramolecular ester group.

摘要

钯(II)催化内炔烃与2-硼苯甲酸甲酯和(2-硼苯基)乙酸甲酯进行环化反应,分别生成2,3-二取代茚满二酮和3,4-二取代2-萘酚。该环化反应通过钯(II)与硼试剂的转金属化以及炔烃的插入反应进行,随后生成的烯基钯(II)物种对分子内酯基进行前所未有的1,2-加成。

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