374818-68-5Relevant articles and documents
Ruthenium-Catalyzed E-Selective Alkyne Semihydrogenation with Alcohols as Hydrogen Donors
Ekebergh, Andreas,Begon, Romain,Kann, Nina
, p. 2966 - 2975 (2020)
Selective direct ruthenium-catalyzed semihydrogenation of diaryl alkynes to the corresponding E-alkenes has been achieved using alcohols as the hydrogen source. The method employs a simple ruthenium catalyst, does not require external ligands, and affords the desired products in > 99% NMR yield in most cases (up to 93% isolated yield). Best results were obtained using benzyl alcohol as the hydrogen donor, although biorenewable alcohols such as furfuryl alcohol could also be applied. In addition, tandem semihydrogenation-alkylation reactions were demonstrated, with potential applications in the synthesis of resveratrol derivatives.
Sonogashira diversification of unprotected halotryptophans, halotryptophan containing tripeptides; and generation of a new to nature bromo-natural product and its diversification in water
Corr,Sharma,Pubill-Ulldemolins,Bown,Poirot,Smith,Cartmell,Abou Fayad,Goss
, p. 2039 - 2046 (2017)
The blending together of synthetic chemistry with natural product biosynthesis represents a potentially powerful approach to synthesis; to enable this, further synthetic tools and methodologies are needed. To this end, we have explored the first Sonogashira cross-coupling to halotryptophans in water. Broad reaction scope is demonstrated and we have explored the limits of the scope of the reaction. We have demonstrated this methodology to work excellently in the modification of model tripeptides. Furthermore, through precursor directed biosynthesis, we have generated for the first time a new to nature brominated natural product bromo-cystargamide, and demonstrated the applicability of our reaction conditions to modify this novel metabolite.
Pd(II)–acylthiourea complex and its immobilized counterpart catalyzed condensation of phenylacetylene with aryl halides
Sindhuja,Vasanthakumar,Karvembu
, (2019/12/25)
New Pd(II) complex, trans-[PdCl2L2] (1) (L = N-carbamothioylthiophene-2-carboxamide), was prepared and characterized. Its heterogeneous counterpart, trans-[PdCl2(L-SNPs)2] (2) (L-SNPs = ligand immobilized on silica nanoparticles), was also prepared through covalent modification of the ligand using silica nanoparticles and characterized. Both 1 and 2 were exploited for their catalytic activity towards condensation of phenylacetylene with aryl halides. The complexes exhibited good activity when aryl halide bears I? or Br? group. Further, catalyst 2 can be reused for four cycles.
Catalytic Activation of Trimethylsilylacetylenes: A One-Pot Route to Unsymmetrical Acetylenes and Heterocycles
Lasányi, Dániel,Mészáros, ádám,Novák, Zoltán,Tolnai, Gergely L.
, p. 8281 - 8291 (2018/06/11)
For the synthesis of unsymmetrical acetylenes, a Sonogashira coupling-deprotection-Sonogashira coupling reaction sequence is often used. Removal of protecting groups requires harsh conditions or an excess of difficult to handle and expensive reagents. Herein, we disclose a novel catalytic method for the selective deprotection of trimethylsilylacetylenes in Sonogashira reaction. The reagent hexafluorosilicic acid, an inexpensive nontoxic compound, was used to promote the selective desilylation. This method enables the efficient synthesis of unsymmetric acetylenes with other silylated functional groups present. Further possibilities of the method were explored by synthesis of heterocycles.
Sonogashira cross-coupling reactions and construction of the indole ring system using a robust, silica-supported palladium catalyst
Tyrrell, Elizabeth,Whiteman, Leon,Williams, Neil
experimental part, p. 829 - 835 (2009/07/25)
The use of a recyclable silica-supported palladium catalyst in Sonogashira couplings and indole syntheses using a range of functionalised substrates is described. The catalyst is shown to be both robust and versatile, effecting the synthesis of 2-phenylindole in quantitative yield without the need for N-protection, a copper co-catalyst, a base, or a solvent. Georg Thieme Verlag Stuttgart.
Synthesis and biological evaluation of new dipyrrolo[3,4-a:3,4-c]carbazole-1,3,4,6-tetraones, substituted with various saturated and unsaturated side chains via palladium catalyzed cross-coupling reactions
Henon, Helene,Anizon, Fabrice,Golsteyn, Roy M.,Leonce, Stephane,Hofmann, Robert,Pfeiffer, Bruno,Prudhomme, Michelle
, p. 3825 - 3834 (2007/10/03)
The syntheses of a series of dipyrrolo[3,4-a:3,4-c]carbazole-1,3,4,6-tetraones, substituted in 10-position with saturated and unsaturated side chains, via palladium catalyzed cross-coupling reactions, are described. These compounds can be considered as granulatimide bis-imide analogues. Their inhibitory activity toward Chk1 kinase and their antiproliferative activities in vitro in four tumor cell lines are reported.
Sonogashira cross-coupling reactions with heteroaryl halides in the presence of a tetraphosphine-palladium catalyst
Feuerstein, Marie,Doucet, Henri,Santelli, Maurice
, p. 1717 - 1720 (2007/10/03)
Heteroaryl halides undergoes cross-couplings with alkynes in good yields in the presence of [PdCl(C3H5)]2/cis,cis,cis-1,2, 3,4-tetrakis(diphenylphosphinomethyl)cyclopentane as catalyst. A variety of heteroaryl halides such as pyridines, quinolines, a pyrimidine, an indole, a thiophene, or a thiazole have been used successfully. The reaction also tolerates several alkynes such as phenylacetylene and a range of alk-1-ynols. Furthermore, this catalyst can be used at low loading with some substrates.
