A site-selective and stereospecific cascade Suzuki–Miyaura annulation of alkyl 1, 2-bisboronic esters and 2, 2′-dihalo 1, 1′-biaryls. Issue 32 (23rd March 2021)

• Record Type: Journal Article
• Authors: Willems, Suzanne; Toupalas, Georgios; Reisenbauer, Julia C.; Morandi, Bill
• Is Part Of: Chemical communications. Volume 57:Issue 32(2021)
• Page Start: 3909
• Page End: 3912
• Publication Date: 2021-03-23
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d1cc00648g
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : A cascade Suzuki–Miyaura cross-coupling between two non-symmetrical coupling partners gave rise to 9, 10-dihydrophenanthrenes with full site-selectivity. The choice of base was critical to facilitate the challenging coupling of the secondary boronate group. 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.