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 Nov 2020
Accepted
17 Dez 2020
First published
29 Dez 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

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