Carbonylative Suzuki Coupling Reaction Catalyzed by a Hydrospirophosphorane Palladium Complex

Wójcik, Przemysław; Sygellou, Labrini; Gniewek, Andrzej; Skarżyńska, Anna; Trzeciak, Anna M.

doi:10.1002/cctc.201700946

Cited by 18 publications

(8 citation statements)

References 65 publications

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“…Wojcik co‐workers [44] reported hydrospirophosphorane ligated Pd‐complex as a catalyst for the carbonylative Suzuki coupling with a variety of aryl iodides 35a and sodium tetraphenyl‐borate as well as arylboronic acids 35b to prepare a sequence of asymmetrical ketones 35c . In this reaction, the hydrospirophosphorane ligand played a double role to stabilize Pd in molecular complexes as well as Pd‐nanoparticles formed in the catalytic system in situ .…”

Section: Palladium Catalysed Carbonylative Suzuki‐miyaura Coupling Rementioning

confidence: 99%

Advances in Transition‐Metal Catalyzed Carbonylative Suzuki‐Miyaura Coupling Reaction: An Update

et al. 2021

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Transition metals have been an indispensable component of modern catalysis and among these palladium is the top‐ranked choice of chemists as a catalyst. After the several important developments of palladium catalysed C−C cross‐coupling reactions, carbonylative transformations have been realised as an attractive post modification of these reactions. Carbonylative Suzuki‐Miyaura coupling reaction is among such transformations for direct incorporation of CO fragment for the preparation of biaryl or aryl/alkyl ketones via transition‐metal catalysis. Ketone functionality is basically a valuable building block having huge pharmaceutical and agrochemical applications. Moreover, carbonylative Suzuki‐Miyaura coupling is also used in the synthesis of various natural bioactive molecules through the direct joining of molecular fragments via CO bridge. In this review, the past decade developments in the carbonylative Suzuki‐Miyaura coupling reactions are documented in detail with modern approaches in transition‐metal catalysis.

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Section: Palladium Catalysed Carbonylative Suzuki‐miyaura Coupling Rementioning

confidence: 99%

Advances in Transition‐Metal Catalyzed Carbonylative Suzuki‐Miyaura Coupling Reaction: An Update

et al. 2021

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“…Nanoparticles probably are stabilized by the excess of tert ‐butyl bromide [ 35 ] and product of the cleavage of HSP ligand, that is, phosphonate moieties, reported elsewhere. [ 6 ]…”

Section: Resultsmentioning

confidence: 99%

“…During our investigations of HSP complexes, we have demonstrated excellent catalytic properties of palladium phosphorane complex [PdCl 2 {P(OCMe 2 CMe 2 O)OC 6 H 4 NH 2 }] in carbonylative Suzuki coupling reaction of substituted iodobenzenes with arylboronic acids and with sodium tetraphenylborate. [ 6 ] We have discovered that palladium complexes appeared to be excellent catalysts for Heck and Hiyama carbon‐carbon coupling, yielding stilbenes with high yield and selectivity. [ 7,8 ] High‐valent oxorhenium hydrospirophosphorane complexes appeared to be co‐catalyst of choice in the oxidation of aldehydes with molecular oxygen in the presence of NHPI as the free‐radical source and catalyst initiator.…”

Section: Introductionmentioning

confidence: 99%

The two faces of platinum hydrospirophosphorane complexes—Not only relevant catalysts but cytotoxic compounds as well

Skarżyńska

Kowalczyk

Majchrzak

et al. 2021

Applied Organom Chemis

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Platinum complexes [PtCl2(L)] L = L1, L2 with symmetrical HP (OCH2CMe2NH)2 (L1) and unsymmetrical HP(OCMe2CMe2O)(OCH2CMe2NH) (L2) hydrospirophosphorane (HSP) ligands were demonstrated to play a dual role of catalysts and cytotoxic compounds as well. The structure of new complex [PtCl2(L2)] was confirmed by physicochemical and spectroscopic methods, as well as single X‐ray diffraction studies for [PtCl2{P (OCMe2CMe2O)(OCH2CMe2NH2)}]. HSP ligand coordinated to the platinum center in bidentate κ2‐P,NH2 chelating mode of fashion. Both complexes were found to exhibit catalytic activity for Heck cross‐coupling reactions of iodobenzene with substituted styrenes, with good conversion and yield of stilbenes. Moreover, complexes have been applied as excellent catalysts for highly regioselective hydrosilylation of aromatic and aliphatic terminal olefins, and acetylenes terminal and internal as well. On the other hand, the preliminary biological studies revealed that in the presence of foretinib, drug candidate in clinical trials for the treatment of cancer, platinum complexes revealed increased synergistic effect and efficiently decreased the number of viable cells of triple negative breast cancer MDA‐MB‐231 cell line.

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“…For instance, the carbonylative Suzuki–Miyaura coupling reactions of aryl boronic acids with 2‐bromopyridine or aryl bromides have been associated with many shortcomings such as high catalyst loading, low yields, and low selectivity. In addition, these reactions need high in situ loading of phosphines 2,28,60,63 . To our knowledge, Pd(II)‐NHC complexes were not largely reported as catalysts in the carbonylative Suzuki–Miyaura coupling reactions of aryl bromides with boronic acids.…”

Section: Resultsmentioning

confidence: 99%

Novel and efficient bridged bis(N‐heterocyclic carbene)palladium(II) catalysts for selective carbonylative Suzuki–Miyaura coupling reactions to biaryl ketones and biaryl diketones

Mansour

Fettouhi

Ali

2020

Applied Organom Chemis

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Bridged N,N′‐substituted bisbenzimidazolium bromide salts (L1, L2, and L3) were synthesized and fully characterized. Reactions of palladium acetate with L1, L2, and L3 afforded corresponding new bridged bis(N‐heterocyclic carbene)palladium(II) complexes (C1, C2, and C3) in high yields. The X‐ray structure of complex C1 showed that the Pd(II) ion is bonded to the two carbon atoms of the bis(N‐heterocyclic carbene) and two bromido ligands are in the cis position, resulting in a distorted square planar geometry. The three Pd(NHC)2Br2 complexes C1, C2, and C3 were evaluated in carbonylative Suzuki–Miyaura coupling reactions of aryl boronic acids with aryl halides and displayed high catalytic activity with low catalyst loading. The coupling reactions of aryl bromides were selective towards the carbonylation product at higher carbon monoxide pressure.

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Carbonylative Suzuki Coupling Reaction Catalyzed by a Hydrospirophosphorane Palladium Complex

Abstract: Conversion4 0%, [b] 4e 39 % Conversion6 8%, [c] 4e 58 %( 50 %) [d] Conversion 44 %, [b] 4f43 % Conversion 60 %, [c] 4f52 %( 40 %) [d] Conversion 60 %, [b] 4g 59 % Conversion 72 %, [c] 4g 71 %(64 %) [d] Conversion 37 %, [b] 4h 37 % Conversion 52 %, [c] 4h 52 %( 44 %) [d]

Cited by 18 publications

References 65 publications

Advances in Transition‐Metal Catalyzed Carbonylative Suzuki‐Miyaura Coupling Reaction: An Update

Advances in Transition‐Metal Catalyzed Carbonylative Suzuki‐Miyaura Coupling Reaction: An Update

The two faces of platinum hydrospirophosphorane complexes—Not only relevant catalysts but cytotoxic compounds as well

Novel and efficient bridged bis(N‐heterocyclic carbene)palladium(II) catalysts for selective carbonylative Suzuki–Miyaura coupling reactions to biaryl ketones and biaryl diketones

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