The Sonogashira Reaction:  A Booming Methodology in Synthetic Organic Chemistry

Shape‐Switchable Azo‐Macrocycles

“…The Sonogashira cross coupling reaction is well known as being one of the most important and utilized reactions for the construction of carbon carbon bonds. [146] This type of reaction is widely applied to introduce divers functional group in organic chemistry, material science and molecular electronics. [136][146] [147] The Sonogashira reaction is a palladium catalyzed coupling reaction with a copper(I) salt as co-catalyst.…”

First examples of functionalisation of meso -aryl tetrabenzotriazaporphyrins (TBTAPs) through cross-coupling reactions

“…The arrangement places the new benzene ring of 2-substituted derivative 7 above the aromatic macrocycle core so that the meta and para protons of the new ring experience a shielding effect and appear around δ 6.4 ppm. The second cross-coupling functionalisation strategy employed Sonagashira cross-coupling, 13 selecting phenylacetylene 10 as reactant. In a typical Sonagashira cross-coupling aryl halides are treated with terminal acetylenes, catalysed by palladium and employing copper as co-catalyst.…”

“…1 H NMR (500 MHz, THF-d8, 298 K): δ (ppm) = 9.60 (d,J = 8.3 Hz,2H),4H),8.32 (d,J = 6.7 Hz,2H),8.25 (d,J = 7.9 Hz,2H),6H),7.91 (t,J = 7.3 Hz,2H),7.66 (t,J = 7.8 Hz,2H),7.59 (t,J = 7.4 Hz,2H),7.52 (t, J = 6.9 Hz, 1H), 7.29 (d, J = 8.1 Hz, 2H). 13 C NMR (125.7 MHz, THF-d8, 298 K): δ (ppm) = 156.59, 153.49, 152.38, 145.16, 143.30, 142.75, 142.15, 141.19, 141.17, 140.94, 140.23, 134.10, 132.25, 130.43, 130.06, 129.75, 129.61, 129.18, 128.41, 127.87, 127.43, 127.09, 125.83, 125.46, 123.86, 123.74, 123.58 A mixture of bromophenyl TBTAP (1.0 eq), BINAP (0.06 equiv) and PdCl2(MeCN)2 (0.07 equiv) was sealed in a microwave vessel with a magnetic bar and then evacuated and backfilled with argon three times. A solution of phenylacetylene (1.6 equiv) and DBU (2.5 equiv) in dry DMF (1.0 mL) was added and stirred under argon for 5 min.…”

Multi-pyridine decorated Fe(ii) and Ru(ii) complexes by Pd(0)-catalysed cross couplings: new building blocks for metallosupramolecular assemblies

“…A suitable means of constructing these structures is via palladium(0)-catalysed Suzuki 15 or Sonogashira couplings. 16 Suzuki coupling between mono-haloterpyridine derivatives 17 and boronic acids or esters, as well as upon their metal complexes is well established, 18 and Sonogashira couplings on polypyridine derivatives have been also reported. 19,20 Herein we report eight new Fe(II) or Ru(II) complexes of 2,2′:6′:2″-terpyridine metal complexes of the type [M(tpy) 2 ] 2+ which feature multiple pendant pyridyl groups (ligands 1-4, Fig.…”