- Development and Mechanistic Study of Quinoline-Directed Acyl C-O Bond Activation and Alkene Oxyacylation Reactions
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The intramolecular addition of both an alkoxy and acyl substituent across an alkene, oxyacylation of alkenes, using rhodium catalyzed C-O bond activation of an 8-quinolinyl ester is described. Our unsuccessful attempts at intramolecular carboacylation of ketones via C-C bond activation ultimately informed our choice to pursue and develop the intramolecular oxyacylation of alkenes via quinoline-directed C-O bond activation. We provide a full account of our catalyst discovery, substrate scope, and mechanistic experiments for quinoline-directed alkene oxyacylation.
- Hoang, Giang T.,Walsh, Dylan J.,McGarry, Kathryn A.,Anderson, Constance B.,Douglas, Christopher J.
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p. 2972 - 2983
(2017/03/23)
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- Pd-Catalyzed regioselective hydroesterification of 2-allylphenols to seven-membered lactones without external CO gas
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Effective Pd-catalyzed regioselective hydroesterification of 2-allylphenols with phenyl formate is described. A variety of seven-membered lactones can be obtained in good yields under mild conditions without the use of toxic CO gas.
- Chang, Wenju,Li, Jingfu,Ren, Wenlong,Shi, Yian
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supporting information
p. 3047 - 3052
(2016/03/19)
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- Structure-activity relationships in the domain of odorants having marine notes
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Continuing our investigations into marine note odorants, we herein describe several new scaffolds. Among them, 2,3-dihydrobenzofuran-2-carbaldehyde is particularly interesting. The results demonstrate that the seven-membered ring with a ketone functional group of the Calone 1951 family can be replaced by a five-membered ring carrying an aldehydefunction. In addition, this work has allowed us to discover the valuable 2-methoxy-4-methylphenyl methyl carbonate (20b), which is very close to vanillin, and 2-methoxy-2,4-dimethyl-1,3-benzodioxole (29d), which belongs to the isoeugenol/dihydroeugenol olfactive family.
- Gaudin, Jean-Marc,De Saint Laumer, Jean-Yves
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p. 1437 - 1447
(2015/03/04)
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- Insertion of an Alkene into an ester: Intramolecular oxyacylation reaction of alkenes through acyl C-O bond activation
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Atom economy and esters: compatible now! The first catalytic insertion of a C-C bond into an acyl C-O bond was achieved using rhodium catalysts (see scheme). The products are β-alkoxy ketones with a fully substituted carbon center. Quinoline chelating groups were employed to stabilize the Rh-alkoxide intermediate.
- Hoang, Giang T.,Reddy, Venkata Jaganmohan,Nguyen, Huy H. K.,Douglas, Christopher J.
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p. 1882 - 1884
(2011/04/16)
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- Pd-Catalyzed intramolecular oxyalkynylation of alkenes with hypervalent iodine
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(Figure presented) The first example of intramolecular oxyalkynylation of nonactivated alkenes using oxidative Pd chemistry is reported. Both phenol and aromatic or aliphatic acid derivatives could be used under operator-friendly conditions (room temperature, technical solvents, under air). The discovery of the superiority of benzlodoxolone-derlved hypervalent iodine reagent 3d as an alkyne transfer reagent further expands the rapidly increasing utility of hypervalent iodine reagents in catalysis and is expected to have important implications for other similar processes.
- Nicolal, Stefano,Erard, Stephane,Gonzalez, Davinla Fernandez,Waser, Jerome
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supporting information; experimental part
p. 384 - 387
(2010/03/04)
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- A room temperature alternative of the Claisen rearrangement route to ortho allylated phenols: Unique reactivity pattern of allylindium reagents
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Quinol ethers and quinone monoketals are shown to undergo formal anti-Michael addition reactions with allylindium reagents at room temperature to give only ortho allylated phenols in good yields.
- Mal, Dipakranjan,Pahari, Pallab,Senapati, Bidyut K.
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p. 2097 - 2100
(2007/10/03)
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- Eine thermische, intramolekulare -Cycloaddition eines Allenyl-allyl-benzols; Synthese von Allenylbenzolen durch saeurekatalysierte Dienol-Benzol-Umlagerung
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A few years ago, it has been shown that the acid-catalyzed dienol-benzene rearrangement of 2-propinyl-substituted cyclohexadienols is a convenient synthesis for allenyl-sunstituted benzene derivatives.The cyclohexadienols 20 and 21 were prepared via C-alk
- Summermatter, Walter,Heimgartner, Heinz
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p. 1298 - 1309
(2007/10/02)
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