Pd-Catalyzed Dynamic Kinetic Asymmetric Cross-Coupling of Heterobiaryl Bromides with N-Tosylhydrazones

Author(s)

Kattela, Shivashankar ; Correia, Carlos Roque D. ; Ros, Abel ; Hornillos, Valentin ; Iglesias-Sigu, Javier ; Fernandez, Rosario ; Lassaletta, Jose M.

• Document type: Journal article
• Source: ORGANIC LETTERS; v. 24, n. 21, p. 5-pg., 2022-06-03.

Abstract

A dynamic kinetic asymmetric Pd-catalyzed cross-coupling reaction of heterobiaryl bromides with ketone N-tosylhydrazones for the synthesis of heterobiaryl styrenes is described. The combination of Pd(dba)(2) as a precatalyst with a TADDOL-derived phosphoramidite ligand provides the corresponding coupling products in good yields and high enantioselectivities under mild conditions. Racemization-free N-oxidation and N-alkylation of the products allowed us to obtain appealing functionalized axially chiral heterobiaryl derivatives. (AU)

• FAPESP's process: 17/10931-2 - Development of substrate controlled asymmetric Suzuki-Miyaura biaryl couplings using chiral N,N-ligands and synthetic potential applications
• Grantee: Shivashankar Kattela
• Support Opportunities: Scholarships abroad - Research Internship - Post-doctor