Stille vs. Suzuki - cross-coupling for the functionalization of diazocines

Melanie Walther; Waldemar Kipke; Raul Renken; Anne Staubitz

doi:10.1039/d3ra02988c

Stille vs. Suzuki - cross-coupling for the functionalization of diazocines

RSC Adv. 2023 May 30;13(23):15805-15809. doi: 10.1039/d3ra02988c. eCollection 2023 May 22.

Authors

Melanie Walther^{1

2}, Waldemar Kipke^{1

2}, Raul Renken¹, Anne Staubitz^{1

2}

Affiliations

¹ University of Bremen, Institute for Analytical and Organic Chemistry Leobener Straße 7 D-28359 Bremen Germany staubitz@uni-bremen.de.
² University of Bremen, MAPEX Center for Materials and Processes Bibliothekstraße 1 D-28359 Bremen Germany.

Abstract

Diazocines are azobenzene derived macrocyclic photoswitches with well resolved photostationary states for the (E)- and (Z)-isomers, which improves their addressability by light. In this work, effective procedures for the stannylation and borylation of diazocines in different positions are reported. Their use in Stille cross-coupling and Suzuki cross-coupling reactions with organic bromides is demonstrated in yields of 47-94% (Stille cross-coupling) and 0-95% (Suzuki cross-coupling), respectively.