Synthesis and resolution of a 1,1′-biazulene analogue of BINOL

Anthony P. Gee; Tiberiu-M. Gianga; Gabriele Kociok-Köhn; G. Dan Pantoş; Simon E. Lewis

doi:10.1039/D5RA02520F

Synthesis and resolution of a 1,1′-biazulene analogue of BINOL

Anthony P. Gee, Tiberiu-M. Gianga, Gabriele Kociok-Köhn, G. Dan Pantoş, Simon E. Lewis

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Abstract

Biaryls exhibiting axial chirality have been extensively exploited in fields such as asymmetric catalysis, but the biaryl linkage typically consists of benzenoid aromatic rings, with non-benzenoid biaryls being scarce. Here we report the first preparation of a (non-benzenoid) 1,1′-biazulene-2,2′-diol (“1,1′-BAzOL”) in enantiopure form and determine its barrier to racemisation. Furthermore we transformed a 1,1′-biazulene-2,2′-diol into the corresponding 2,2′-bis(phosphonate), thereby demonstrating functional group interconversion through cross coupling and highlighting the potential for diversification.

Original language	English
Pages (from-to)	14881-14892
Number of pages	12
Journal	RSC Advances
Volume	15
Issue number	19
Early online date	16 May 2025
DOIs	https://doi.org/10.1039/D5RA02520F
Publication status	Published - 31 Dec 2025

Data Availability Statement

The data supporting this article have been included as part of the ESI.† Crystallographic data for both diastereoisomers of 22 and for 1,1′-BAzOL (Ra)-20 have been deposited at the CCDC under #2421193–2421195 and can be obtained free of charge at https://www.ccdc.cam.ac.uk/structures.

Funding

We thank EPSRC for a DTP PhD studentship to A. P. G. We acknowledge the research facilities at the University of Bath (https://doi.org/10.15125/mx6j-3r54).

Funders	Funder number
Engineering and Physical Sciences Research Council

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10.1039/D5RA02520FLicence: CC BY

___RSC_Adv__2025_15_14881___Final published version, 1.66 MBLicence: CC BY

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AU - Kociok-Köhn, Gabriele

AU - Pantoş, G. Dan

AU - Lewis, Simon E.

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AB - Biaryls exhibiting axial chirality have been extensively exploited in fields such as asymmetric catalysis, but the biaryl linkage typically consists of benzenoid aromatic rings, with non-benzenoid biaryls being scarce. Here we report the first preparation of a (non-benzenoid) 1,1′-biazulene-2,2′-diol (“1,1′-BAzOL”) in enantiopure form and determine its barrier to racemisation. Furthermore we transformed a 1,1′-biazulene-2,2′-diol into the corresponding 2,2′-bis(phosphonate), thereby demonstrating functional group interconversion through cross coupling and highlighting the potential for diversification.

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ER -

Synthesis and resolution of a 1,1′-biazulene analogue of BINOL

Abstract

Data Availability Statement

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