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A site-selective and stereospecific cascade Suzuki–Miyaura annulation of alkyl 1,2-bisboronic esters and 2,2′-dihalo 1,1′-biaryls

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Willems,  Suzanne
Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Morandi,  Bill
Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Laboratorium für Organische Chemie ETH Zürich;

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Citation

Willems, S., Toupalas, G., Reisenbauer, J. C., & Morandi, B. (2021). A site-selective and stereospecific cascade Suzuki–Miyaura annulation of alkyl 1,2-bisboronic esters and 2,2′-dihalo 1,1′-biaryls. Chemical Communications, 57(32), 3909-3912. doi:10.1039/D1CC00648G.


Cite as: http://hdl.handle.net/21.11116/0000-0008-54FC-E
Abstract
A cascade Suzuki–Miyaura cross-coupling giving rise to 9,10-dihydrophenanthrenes has been developed. Using biaryls with unsymmetrical substitution-pattern full site-selectivity was observed. Furthermore, this cross-coupling of an alkyl 1,2-bisboronic pinacol ester proceeds through the challenging coupling of a secondary boronate with complete stereoretention.