Activation and Catalytic Reactions of Saturated Hydrocarbons in the Presence of Metal Complexes
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Carbon-carbon or carbon-heteroatom cross-coupling reactions catalyzed by transition metal catalysts have been widely investigated and established because of their significance in organic synthesis. In particular, homogeneous Pd catalysis has been well studied in the most powerful and versatile synthetic process such as Heck [ 1 ] , Suzuki [ 2 ] , Stille [ 3 ] , Sonogashira [ 4 ] , Negishi [ 5 ] , and Buchwald-Hartwig reactions [ 6 ].
Alternatively, the more desirable direct functionalization of hydrocarbons via C-H bond activation has still remained a challenge in cross-coupling reactions. In recent years, a substantial number of metal complexes that are able to selectively activate C-H bonds under mild conditions have been discovered.
Additionally, the C-H bond activation is often inhibited by water or by the product eliminated from the metal complex during the reaction. Such reactions have been studied in heterogeneous Pd catalytic systems but are rarely observed in homogeneous Pd systems. To further investigate the C-H activation of this class of Pd complexes, we extended the structural motifs of palladium to various tridentate ligands.
To circumvent the dimerization of monomeric species in aqueous solution at low temperatures, we employed a methyl ether 7a or benzyl ether 7b group instead of the previously employed hydroxyl moiety as oxygen-site of the ligands Scheme 1.
Compounds 4a and 4b were prepared from ethanolamine and valinol, respectively. Amide compound 9 was easily derived from aniline and bromoacetyl bromide. In addition, longer reaction times may not affect the catalytic cycle dramatically entry 3.
As shown in Figure 1 B , the signal for benzene-d 6 decreased in intensity over a period of 16 h. Overall conversion of C 6 D 6 to C 6 H 6 by 3. REF 1 internal standard : poly dimethylsiloxane. In general, effective multiple deuterium incorporation into the alkyl C-H was observed with D 2 O as both the solvent and deuterium source. Table 2 lists the organic substrates examined and their corresponding extents of deuterium incorporation. Catalyst 8a showed deuteration ability for a wide range of molecules including saturated hydrocarbons, ethers, and ketones.
Ether compounds such as THF and diethyl ether showed lower levels of D-incorporation compared to aromatic and saturated hydrocarbons, however we observed that it was also a facile process with catalyst 8a under conditions of higher temperatures and longer reaction times entries 6 and 8 with increased catalyst loading entry 9. Also, we examined the deuterium incorporation of toluene in D 2 O to elucidate the possibility of selective C-H activation for aryl and alkyl groups.
We detected the oxidation product of phenol via C-H activation to afford phenol as a product. Importantly, the catalytic reaction was not inhibited by coordination of water to Pd. Strongly electron donating groups such as NHC, amide N, and O would increase the electron density of Pd, allowing a weak interaction between electrophilic Pd and water. In addition, we were able to obtain a preliminary result for the direct functionalization in aqueous media. This independent character of the developed catalysts from water and polar solvents can open up a new avenue in Pd II catalysis.
Accordingly, utilization of this system for the incorporation of deuterium and other useful functional groups into the C-H bonds of numerous classes of organic compounds will be extensively pursued and reported in due course.
Pd cation compounds were prepared when required. Catalyst 7a , 7b , or 11 and 1. After passing through celite column, The filtrate was dried in a rotary evaporator. The dried compound was dissolved in 0. Deuteration levels were monitored by 1 H NMR using an external capillary standard consisting of a solution of the poly dimethylsiloxane. Pd cationic compound 2 was prepared when required. The catalyst 1 2 mg, 0.zidowntelligh.tk
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Recent Activity. The snippet could not be located in the article text. This may be because the snippet appears in a figure legend, contains special characters or spans different sections of the article. Adv Synth Catal. Author manuscript; available in PMC Mar 9. PMID: Olsen , a Satoshi Sakaguchi , b G.
Janet M. Surya Prakash. Copyright notice. See other articles in PMC that cite the published article. Abstract While developing novel catalysts for carbon-carbon or carbon-heteroatom coupling N, O, or F , we were able to introduce tridentate NHC-amidate-alkoxide palladium II complexes.
An efficient organocatalytic method for constructing biaryls through aromatic C–H activation
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Georgiy B. Shul'pina c. You have access to this article. Please wait while we load your content Something went wrong. Try again? Cited by. Back to tab navigation Download options Please wait Article type: Minireview. DOI: Download Citation: Catal. Oxidative functionalization of C—H compounds induced by the extremely efficient osmium catalysts a review G. Shul'pin, M.