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

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

Melanie Walther  1   2 , Waldemar Kipke  1   2 , Raul Renken  1 , Anne Staubitz  1   2
Affiliations

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

Melanie Walther et al. RSC Adv. .

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.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Scheme 1
Scheme 1. Cross-coupling reaction of diazocines.
Scheme 2
Scheme 2. Synthesis of stannylated 3–4 and borylated diazocines 5–6.
Scheme 3
Scheme 3. Scope of Stille and Suzuki cross-coupling reactions for para-substituted diazocines 3 and 5.
Scheme 4
Scheme 4. Side reactions of Suzuki cross-coupling.
Scheme 5
Scheme 5. Scope of Stille and Suzuki cross-coupling reactions for meta-substituted diazocines 4 and 6.
See this image and copyright information in PMC

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