Chemical and Pharmaceutical Bulletin
The Pharmaceutical Society of Japan, established in 1880, is one of Japan’s oldest and most distinguished academic societies. The Society currently has around 18,000 members. It publishes three monthly scientific journals. Chemical and Pharmaceutical Bulletin (Chem. Pharm. Bull.) began publication in 1953 as Pharmaceutical Bulletin. It covers chemistry fields in the pharmaceutical and health sciences. Biological and Pharmaceutical Bulletin (Biol. Pharm. Bull.) began publication in 1978 as the Journal of Pharmacobio-Dynamics. It covers various biological topics in the pharmaceutical and health sciences. A fourth Society journal, the Journal of Health Science, was merged with Biol. Pharm. Bull. in 2012. Yakugaku Zasshi (Japanese for “Pharmaceutical Science Journal”) has the longest history, with publication beginning in 1881. Yakugaku Zasshi is published mostly in Japanese, except for some articles related to clinical pharmacy and pharmaceutical education, which are published in English.
The main aim of the Society’s journals is to advance the pharmaceutical sciences with research reports, information exchange, and high-quality discussion. The average review time for articles submitted to the journals is around one month for first decision. The complete texts of all of the Society’s journals can be freely accessed through J-STAGE. The Society’s editorial committee hopes that the content of its journals will be useful to your research, and also invites you to submit your own work to the journals.

Chairman of Committee
Ken-ichi Hosoya
Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama

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26,962 registered articles
(updated on May 28, 2017)
Online ISSN : 1347-5223
Print ISSN : 0009-2363
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Volume 65 (2017) Issue 5 Pages 409-425
Palladium(0)-Catalyzed Benzylic C(sp3)–H Functionalization for the Concise Synthesis of Heterocycles and Its Applications

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.

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Editor’s picks

This review summarizes author’s recent reports on Pd(0)-catalyzed benzylic C(sp3)-H functionalization for the synthesis of various heterocycles including oxindoles, spirooxindoles, 2-arylindoles, benzocarbazoles, indolocarbazoles, and indoloquinazolinones. The key feature would be a chemoselective C(sp3)-H activation in the oxindole synthesis. The developed method was successfully applied to the total synthesis of several pyrrolophenanthridine alkaloids as well as a synthesis of the right-hand fragment of benzohopane.

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