Synthesis of Bicyclo[1.1.1]pentane (BCP)‐Based Straight‐Shaped Diphosphine Ligands**

Author:

Takano Hideaki12ORCID,Katsuyama Hitomi12ORCID,Hayashi Hiroki12ORCID,Harukawa Miyu3,Tsurui Makoto3,Shoji Sunao13ORCID,Hasegawa Yasuchika13ORCID,Maeda Satoshi1245ORCID,Mita Tsuyoshi12ORCID

Affiliation:

1. Institute for Chemical Reaction Design and Discovery (WPI-ICReDD) Hokkaido University Kita 21, Nishi 10, Kita-ku Sapporo Hokkaido 001-0021 Japan

2. JST ERATO Maeda Artificial Intelligence in Chemical Reaction Design and Discovery Project Kita 10, Nishi 8, Kita-ku Sapporo Hokkaido 060-0810 Japan

3. Faculty of Engineering Hokkaido University Kita 13, Nishi 8, Kita-Ku Sapporo Hokkaido 060-8628 Japan

4. Department of Chemistry Faculty of Science Hokkaido University Kita 10, Nishi 8, Kita-ku Sapporo Hokkaido 060-0810 Japan

5. Research and Services Division of Materials Data and Integrated System (MaDIS) National Institute for Materials Science (NIMS) Tsukuba Ibaraki 305-0044 Japan

Abstract

Abstract[1.1.1]Propellane, which is structurally simple and compact, exhibits promising potential for the synthesis of disubstituted straight‐shaped bicyclo[1.1.1]pentane (BCP) compounds by manipulation of its highly reactive internal C−C bond. BCPs are considered to be isosteres of 1,4‐disubstituted benzenes, which have found broad applications in the areas of functional molecules and drug discovery. The internal C−C single bond of [1.1.1]propellane is regarded as a charge‐shift bond, which can be readily cleaved by radical means to construct BCPs. We herein report a novel synthetic method for (un)symmetric diphosphines based on the BCP motif, which can be interpreted as isosteres of 1,4‐bis(diphenylphosphino)benzenes. The obtained BCP‐diphosphine derivatives were used to generate a straight‐shaped Au complex and an Eu‐based coordination polymer.

Funder

Exploratory Research for Advanced Technology

Japan Society for the Promotion of Science

Uehara Memorial Foundation

Naito Foundation

Publisher

Wiley

Subject

General Medicine

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