New strategy for synthesising conjugated hexatrienylferrocenes via cross-dimerisation

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CMe (1a), with ( E )-butadien-1-ylboronic acid pinacolato ester, CH 2 CH–CHCHB(pin) (2g), yie...

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Bibliographic Details
Published in:New journal of chemistry 2021-09, Vol.45 (33), p.14988-14998
Main Authors: Sawasaki, Asami, Komine, Nobuyuki, Kawauchi, Susumu, Hirano, Masafumi
Format: Article
Language:English
Subjects:
Couplings
Density functional theory
Dienes
Iodides
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Summary: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CMe (1a), with ( E )-butadien-1-ylboronic acid pinacolato ester, CH 2 CH–CHCHB(pin) (2g), yields a conjugated triene, (1 E ,3 E ,5 E )-FcCHCMe–CHCH–CH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 (1 E ,3 E ,5 E )-FcCHCMe–CHCH–CH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.
ISSN:1144-0546
1369-9261
DOI:10.1039/D0NJ05413E