| 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 |
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|
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
Kamura, Kumiko
Yamamoto, Yohsuke
Akiba, Kin-ya
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| アクセス権 |
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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 |
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|
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 |
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|
主題Scheme |
NDC |
|
主題 |
430 |
| 内容記述 |
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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 |
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|
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 |
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|
識別子タイプ |
DOI |
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|
関連識別子 |
10.1002/1521-3765(20020703)8:13<2976::AID-CHEM2976>3.0.CO;2-G |
| 関連情報 |
|
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|
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 |
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収録物識別子タイプ |
ISSN |
|
収録物識別子 |
0947-6539 |
| 収録物識別子 |
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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 |
ChemEurJ_8_2976.pdf (848.2 KB)
