The effect of some additives on the Stille Pd0-catalyzed cross-coupling reaction

Gronowitz, Salo; Björk, Patrick; Malm, Johan; Hörnfeldt, Anna‐Britta

doi:10.1016/0022-328x(93)80368-l

Cited by 103 publications

(36 citation statements)

References 13 publications

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“…The first approach can be achieved by an assortment of reactions often involving palladium-catalysed reactions, for example, Suzuki-Miyaura, 3 Stille, 43 Kumada 44 or Negishi 45 reactions with substituted 2-or 4-halo-pyridines or 2-chloropyridines. To date, synthesis of the ppy ligand can be broken down into two main strategies: (i) modifying an existing pyridine ring or (ii) forming the central pyridine ring with the desired substituents attached.…”

Section: Introductionmentioning

confidence: 99%

The use of organolithium reagents for the synthesis of 4-aryl-2-phenylpyridines and their corresponding iridium(iii) complexes

et al. 2016

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A versatile palladium-free route for the synthesis of 4-aryl-substituted phenylpyridines (ppy), starting from tert-butyl 4-oxopiperidine-1-carboxylate, is reported. Reaction with an aryllithium, followed by trifluoroacetic acid dehydration/deprotection and oxidation with 2-iodoylbenzoic acid and finally phenylation, gave 4 ligands (L(1-4)H): 2,4-diphenylpyridine, 4-(4-methoxyphenyl)-2-phenylpyridine, 2-phenyl-4-(o-tolyl)pyridine and 4-mesityl-2-phenylpyridine. These ligands were coordinated to iridium to give the corresponding Ir(L)2(A) complexes (Ir1-7), where A = ancillary ligand acetylacetate or 2-picolinate. This was used to demonstrate that, through a combination of ancillary ligand choice and torsional twisting between the 4-aryl substituents of the ppy ligands, it is possible to tune the phosphorescent emission of the complexes in the range 502-560 nm.

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Section: Introductionmentioning

confidence: 99%

The use of organolithium reagents for the synthesis of 4-aryl-2-phenylpyridines and their corresponding iridium(iii) complexes

et al. 2016

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“…Exclusive mono-selectivity was observed for all the scaffolds under the present reaction conditions.T he scope of the reaction was explored using various alkenyl alcohols (1g-j)a nd arenes containing different substituents (1k-n). [10,13] With the optimized reaction conditions in hand, we probed various scaffolds having longer alkyl backbones (Scheme 2). [10] Arylnitrile is ak ey structural motif in natural products and pharmaceuticals,a nd provides ap recursor for several valuable compounds because of the transformation of the nitrile into other functionalities.…”

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confidence: 99%

Diverse meta‐C−H Functionalization of Arenes across Different Linker Lengths

et al. 2018

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Arenes containing conformationally flexible long alkylchains have been successfully functionalizedatthe metaposition. Good to excellent meta selectivity is achieved for systems with up to 20 atoms between the target CÀHbond and the coordinating heteroatom of the directing group.T he palladium-catalyzed functionalization reactions include alkylation, cyanation, olefination, and acetoxylation. The meta selectivity is exclusively governed by the design of flexible pyrimidine-based scaffolds.

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“…129 The effects of silver(I) and copper(II) salts on the formation of thiazole-pyridine derivatives was investigated by Gronowitz et al (Scheme 56). 130,131 The use of copper(II) oxide to facilitate the coupling reaction of silylated diaminopurine derivatives with furyl-and thienylstannanes (Scheme 57) was found to result in improved yields in combination with a bidentate phosphine ligand. 132,133 Triphenylarsine (Scheme 58) has also been utilized as a ligand for palladium in Stille couplings of purine derivatives for the preparation of agents for treatment of sleeping sickness.…”

Section: Stille Cross-coupling Reactionsmentioning

confidence: 99%