Sonogashira coupling with aqueous ammonia directed to the synthesis of azotolane derivatives

Abstract

Sonogashira coupling with aqueous ammonia is tolerable for the reaction of aryl iodides or terminal alkynes bearing an azobenzene group. The reaction of (4-heptyloxyphenyl)ethyne with (4heptyloxyphenyl)-(4-iodophenyl)diazene in the presence of 1 mol % of PdCl 2 (PPh 3) 2 , 2 mol % of CuI, and 2 equivalents of 0.5 M aqueous ammonia gives the corresponding azotolane in 87% isolated yield after stirring at room temperature for 15 h.

A Modular Approach for the Synthesis of Nanometer-Sized Polynitroxide Multi-Spin Systems

“…As this route proved to be low-yielding, it was decided to investigate an alternative synthetic path (Scheme , route B). In this case, 4-hydroxy-4′-iodobiphenyl 16 was first reacted with 1,3-diethynylbenzene 18 under aqueous ammonia Sonogashira cross-coupling conditions to afford bis-phenol 22 in 69% yield . The use of these mild Sonogashira conditions was particularly important as it allowed the coupling to proceed in good yield without the use of a protecting group for the phenol.…”

Reduction of Solid-Supported Olefins and Alkynes

“…4-(Phenylethynyl)phenol ( 6a) was prepared through Sonogashira coupling of 4-iodophenol with phenylacetylene . This substrate was then anchored to Merrifield resin ( 10 ) to provide resin-bound 4-(phenylethynyl)phenol ( 6b ).…”

Synthesis and Shuttling Behavior of [2]Rotaxanes with a Pyrrole Moiety

“…Reagents were commercially available and used without further purification unless otherwise noted. Compounds 1 , 5 , 10 , 12 , 13 , 14 , 15 , 16 , 18 , and 21 were prepared by the reported procedure. Chemical shifts were reported in delta units (δ) relative to chloroform (7.24 ppm for 1 H NMR and 77.23 ppm for 13 C NMR).…”