Issue 33, 2021

New strategy for synthesising conjugated hexatrienylferrocenes via cross-dimerisation

Abstract

The first broadly applied strategy for the cross-dimerisation of an internal alkynylferrocene (1) with conjugated dienes (2) is revealed. The Ru(0)-catalysed cross-dimerisation of 1-propynylferrocene, FcC[triple bond, length as m-dash]CMe (1a), with (E)-butadien-1-ylboronic acid pinacolato ester, CH2[double bond, length as m-dash]CH–CH[double bond, length as m-dash]CHB(pin) (2g), yields a conjugated triene, (1E,3E,5E)-FcCH[double bond, length as m-dash]CMe–CH[double bond, length as m-dash]CH–CH[double bond, length as m-dash]CHB(pin) (3ag), in a 92% yield. Subsequently, the Pd(II)-catalysed cross-couplings of 3ag with a series of aryl iodides yields corresponding conjugated polyenes, such as (1E,3E,5E)-FcCH[double bond, length as m-dash]CMe–CH[double bond, length as m-dash]CH–CH[double bond, length as m-dash]CHAr. The photo-electronic properties of the ferrocenyl conjugated polyenes are evaluated and their electronic properties are also evaluated by time-dependent density-functional theory calculations.

Graphical abstract: New strategy for synthesising conjugated hexatrienylferrocenes via cross-dimerisation

Supplementary files

Article information

Article type
Paper
Submitted
04 Pun 2020
Accepted
17 Tsh 2020
First published
29 Tsh 2020

New J. Chem., 2021,45, 14988-14998

New strategy for synthesising conjugated hexatrienylferrocenes via cross-dimerisation

A. Sawasaki, N. Komine, S. Kawauchi and M. Hirano, New J. Chem., 2021, 45, 14988 DOI: 10.1039/D0NJ05413E

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements