Synthesis of Acid Halides, Anhydrides and Related Compounds

Sustmann, Reiner

doi:10.1016/b978-0-08-052349-1.00160-8

Cited by 9 publications

(1 citation statement)

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“…Acid halides are an important class of carbonyl compounds which are widely used as acyl reagents or intermediates to produce numerous carbony compounds 49 . Conventional synthesis of acid halides from transformations of C-H bonds usually undergo carboxylation or oxidation to generate the carboxylic acids, and then react with halogenating reagents, such as PCl 3 , thionyl or oxalyl chloride, to produce the corresponding acyl chlorides, which generate a large amount of wastes 50 .…”

Section: Resultsmentioning

confidence: 99%

Enhancing stability by trapping palladium inside N-heterocyclic carbene-functionalized hypercrosslinked polymers for heterogeneous C-C bond formations

Yue

Xing

Sun

et al. 2020

Preprint

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Catalyst deactivation caused by the aggregation of active metal species in the reaction process poses great challenges for practical applications of supported metal catalysts in solid-liquid catalysis. Herein, we developed a hypercrosslinked polymer integrated with N-heterocyclic carbene (NHC) as bifunctional support to stabilize palladium in heterogeneous C-C bond formations. This polymer supported palladium catalyst exhibits excellent stability in the one-pot fluorocarbonylation of indoles to four kinds of valuable indole-derived carbonyl compounds in cascade or sequential manner, as well as the representative Suzuki-Miyaura coupling reaction. Stabilizing mechanism investigations disclose that this catalyst displays a molecular fence effect in which the coordination of NHC sites and confinement of polymer skeleton contribute together to stabilize the active palladium species in the reaction process. This work provides new insight into the development of supported metal catalysts with high stability and will also boost their efficient applications in advanced synthesis.

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Section: Resultsmentioning

confidence: 99%

Enhancing stability by trapping palladium inside N-heterocyclic carbene-functionalized hypercrosslinked polymers for heterogeneous C-C bond formations

Yue

Xing

Sun

et al. 2020

Preprint

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Synthesis of Monodisperse Macromolecular Bicyclic and dendritic compounds from (R)‐3‐hydroxybutanoic acid and benzene‐1,3,5‐tricarboxylic acid and analysis by fragmenting MALDI‐TOF mass spectroscopy

Seebàch¹,

Herrmann

Lengweiler

et al. 1997

Helvetica Chimica Acta

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Dedicated to Professor Waldemur Adam on the occasion of his 60th birthday(1 1 N.97)As previously shown, oligo-and poly(p-hydroxyalkanoates) have a high tendency to form lamellar crystallites with ca. 50-8, thickness which corresponds to chain lengths of 16 units (Fig. f). To have monodisperse model compounds, we have now prepared bicyclic derivatives with three parallel (27-29) or two parallel and an antiparallel chain (68-70) consisting of up to 16 3-hydroxybutanoate (3-HB) units. We also prepared dendritic compounds (71 -75,82-85) containing oligo(3-HB) chains which cannot possibly be arranged as in the lamellue; the branching units were prepared from trimesic acid (= benzene-l,3,5-tricarboxylic acid). So far, none of the prepared samples formed crystals or contained crystalline domains which would have been suitable for single-crystal or powder-diffraction X-ray analysis. The terminally deprotected dendrimers (74,75, and 85) are multi-anionic (up to 12 peripheral CO,H groups) and biodegradable. The macromolecular HB derivatives (molecular weight up to 10150 Da) have been fully characterized by IR, 'H-and I3C-NMR, [a],, and elemental analysis. Especially important is the analysis by mass spectrometry with the MALDI-TOF technique (Fig. 2), proving that the products are monodisperse; application of a new variation of this MS method (post source decay = PSD or fragment analysis by structural rime of flight = FASTTM) allows for the observation of metastable fragment ions and, thus, is a tool for structural oligomer analysis (Fig. 3). 1. Introduction. -Poly(P-hydroxyalkanoates) (PHAs), an ubiquitous class of biopolymers [2] have been the subject of research in our group for many years [3]. Besides their occurrence as a high-molecular-weight storage material (sPHA) in microorganisms [4] PHAs have also been found in a low-molecular-weight form (cPHA). Reusch and coworkers have shown that low-molecular-weight poly[(R)-3-hydroxybutanoic acid] (P(3-HB) = PHB), ca. 150 units) and CaPP, (calcium polyphosphate) form a complex which may function as an ion channel in genetically competent E. coZi cells [5] [6]. P(3-HB) has also been detected in eucaryotic cells, in human aorta tissue [6], and in blood plasma [5b]. From most of these sources, cPHB and its homolog cPHV (V = valerate = pentanoate) could be extracted with CHC1, and characterized by NMR spectroscopy [6]. Most recently, however, much larger quantities of PHB and PHV have been detected (by degradation to crotonic acid (= but-2-enoic acid) at higher temperature and/or larger reaction times [7], or by transesterifying conversion to ethyl (R)-3-

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Nucleophilic Substitution Reactions at the Carboxyl Carbon

2010

Organic Mechanisms

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Synthesis of Acid Halides, Anhydrides and Related Compounds

Cited by 9 publications

References 123 publications

Enhancing stability by trapping palladium inside N-heterocyclic carbene-functionalized hypercrosslinked polymers for heterogeneous C-C bond formations

Enhancing stability by trapping palladium inside N-heterocyclic carbene-functionalized hypercrosslinked polymers for heterogeneous C-C bond formations

Synthesis of Monodisperse Macromolecular Bicyclic and dendritic compounds from (R)‐3‐hydroxybutanoic acid and benzene‐1,3,5‐tricarboxylic acid and analysis by fragmenting MALDI‐TOF mass spectroscopy

Nucleophilic Substitution Reactions at the Carboxyl Carbon

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