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Synthesis of a Novel Potential Tridentate Anthracene Ligand, 1,8-Bis(dimethylamino)-9-bromoanthracene, and Its Application as Chelate Ligand for Synthesis of the Corresponding Boron and Palladium Compounds

https://hiroshima.repo.nii.ac.jp/records/2006631
https://hiroshima.repo.nii.ac.jp/records/2006631
a7a42948-ff9c-41ac-8b51-872cf2484808
名前 / ファイル ライセンス アクション
ChemEurJ_8_2976.pdf ChemEurJ_8_2976.pdf (848.2 KB)
Item type デフォルトアイテムタイプ_(フル)(1)
公開日 2023-03-18
タイトル
タイトル Synthesis of a Novel Potential Tridentate Anthracene Ligand, 1,8-Bis(dimethylamino)-9-bromoanthracene, and Its Application as Chelate Ligand for Synthesis of the Corresponding Boron and Palladium Compounds
言語 en
作成者 Yamashita, Makoto

× Yamashita, Makoto

en Yamashita, Makoto

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Kamura, Kumiko

× Kamura, Kumiko

en Kamura, Kumiko

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Yamamoto, Yohsuke

× Yamamoto, Yohsuke

en Yamamoto, Yohsuke

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Akiba, Kin-ya

× Akiba, Kin-ya

en Akiba, Kin-ya

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アクセス権
アクセス権 open access
アクセス権URI http://purl.org/coar/access_right/c_abf2
権利情報
権利情報 Copyright (c) 2002 WILEY-VCH Verlag GmbH, Weinheim, Fed. Rep. of Germany
主題
主題Scheme Other
主題 anthracene
主題
主題Scheme Other
主題 boron
主題
主題Scheme Other
主題 N ligands
主題
主題Scheme Other
主題 palladium
主題
主題Scheme NDC
主題 430
内容記述
内容記述 A novel potential tridentate ligand, 1,8-bis(dimethylamino)-9-bromoanthracene, was synthesized. The key steps are as follows: 1) dimethylamination of 1,8-dibromo-9-methoxyanthracene by a modified Buchwald's method to afford 1,8-bis(dimethylamino)-9-methoxyanthracene, and 2) reduction of the methoxy group by LDBB (lithium di-tert-butylbiphenylide) followed by treatment with BrCF2CF2Br. The corresponding 1,8-bis(dimethylamino)-9-lithioanthracene, which should be a useful versatile tridentate ligand, could be generated by treatment of the bromide with one equivalent of nBuLi. The lithioanthracene reacted with B-chloroborane derivatives to give three 9-boryl derivatives. Although we recently reported that the crystal structure of 1,8-dimethoxy-9-B-catecholateborylanthracene was a symmetrical compound with the almost identical two OB distances (2.379(2) and 2.441(2) Å), the newly prepared 1,8-bis(dimethylamino)-9-borylanthracene derivatives clearly have unsymmetrical structures with coordination of only one NMe2 group toward the central boron atom. However, the energy difference between the unsymmetrical and symmeterical structures was found to be very small based on 1H NMR measurements, in which symmetrical anthracene patterns in the aromatic region (two kinds of doublets and a triplet) and a sharp singlet signal of the two NMe2 groups were observed even at -80 ーC. 1,8-Bis(dimethylamino)-9-bromoanthracene itself can be a versatile ligand for transition metal compounds. In fact, direct palladation of the bromide took place by the reaction with [Pd2(dba)3]CHCl3 in THF to give the 9-palladated product. X-ray crystallographic analysis of the Pd compound showed that the square planar palladium atom was coordinated in a symmetrical fashion by both NMe2 groups (PdN bonds are 2.138(5) and 2.146(5) Å).
言語 en
出版者
出版者 Wiley-VCH Verlag GmbH
言語
言語 eng
資源タイプ
資源タイプ識別子 http://purl.org/coar/resource_type/c_6501
資源タイプ journal article
出版タイプ
出版タイプ AO
出版タイプResource http://purl.org/coar/version/c_b1a7d7d4d402bcce
関連情報
識別子タイプ DOI
関連識別子 10.1002/1521-3765(20020703)8:13<2976::AID-CHEM2976>3.0.CO;2-G
関連情報
識別子タイプ DOI
関連識別子 http://dx.doi.org/10.1002/1521-3765(20020703)8:13<2976::AID-CHEM2976>3.0.CO;2-G
収録物識別子
収録物識別子タイプ ISSN
収録物識別子 0947-6539
収録物識別子
収録物識別子タイプ NCID
収録物識別子 AA11076269
開始ページ
開始ページ 2976
書誌情報 Chemistry - A European Journal
Chemistry - A European Journal

巻 8, 号 13, p. 2976-2979, 発行日 2002
旧ID 21527
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