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タイトル: Palladium(0)-catalyzed benzylic C(sp³)-H functionalization for the concise synthesis of heterocycles and its applications
著者: Tsukano, Chihiro  kyouindb  KAKEN_id
著者名の別形: 塚野, 千尋
キーワード: C–H functionalization
palladium (Pd)
oxindole
heterocycle
total synthesis
発行日: 1-May-2017
出版者: Pharmaceutical Society of Japan
誌名: Chemical and Pharmaceutical Bulletin
巻: 65
号: 5
開始ページ: 409
終了ページ: 425
抄録: C-H functionalization reactions involve the activation of otherwise unreactive C-H bonds, and represent atom economical methods for the direct transformation of simple substrates to complex molecules. While transition metal-catalyzed C(sp²)-H functionalization reactions are regularly used in synthesis, C(sp³)-H functionalization is rarely applied to the synthesis of complex natural products because of the difficulties associated with controlling selectivity. With this in mind, we focused on the development of new palladium (Pd)(0)-catalyzed C(sp³)-H functionalization reactions for the synthesis of complex molecules, resulting in several new methods capable of solving these problems. We initially developed a concise synthetic method for the facile construction of oxindoles and spirooxindoles via a Pd-catalyzed benzylic C(sp³)-H functionalization reaction. This method was subsequently extended to the synthesis of various heterocycles, including 2-arylindoles, benzocarbazole, indolocarbazole, indoloquinazolinone, and indoloquinazolinedione, as well as the total synthesis of several pyrrolophenanthridine alkaloids without the need for any protecting groups. This method was also successfully applied to the synthesis of the right-hand fragment of benzohopane from tetrahydro-2H-fluorene, which was constructed by a Pd-catalyzed benzylic C(sp³)-H functionalization. In this review, we provide a detailed discussion of our most recent investigations pertaining to Pd(0)-catalyzed benzylic C(sp³)-H functionalization.
著作権等: 許諾条件に基づいて掲載しています。
URI: http://hdl.handle.net/2433/235958
DOI(出版社版): 10.1248/cpb.c16-00969
PubMed ID: 28458363
出現コレクション:学術雑誌掲載論文等

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