Synthesis of Bicyclo[1.1.1]pentane (BCP)‐Based Straight‐Shaped Diphosphine Ligands**-Reference-Cited by-同舟云学术

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

Published:2023-04-20 Issue:23 Volume:135 Page:
ISSN:0044-8249
Container-title:Angewandte Chemie
language:en
Short-container-title:Angewandte Chemie

Author:

Takano Hideaki¹²^ORCID,Katsuyama Hitomi¹²^ORCID,Hayashi Hiroki¹²^ORCID,Harukawa Miyu³,Tsurui Makoto³,Shoji Sunao¹³^ORCID,Hasegawa Yasuchika¹³^ORCID,Maeda Satoshi¹²⁴⁵^ORCID,Mita Tsuyoshi¹²^ORCID

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

Link

https://onlinelibrary.wiley.com/doi/pdf/10.1002/ange.202303435

Reference50 articles.

1. Ligand Bite Angle Effects in Metal-catalyzed C−C Bond Formation

3. Organometallic polymers with gold(I) centers bridged by diphosphines and diacetylides

4. Synthesis and Crystal Structure Determination of Bifunctional Phosphine-Linked Triplatinum Double-Cluster Complexes

5. Ligand connected metal clusters. The molecular structures and solid state packing of {Ru3(CO)11}2(bis(diphenylphosphino)ethane) and {Ru3(CO)11}2(1,4-bis(diphenylphosphino)benzene)