ChemInform Abstract: Palladium-Catalyzed Double Arylations of Terminal Olefins in Acetic Acid.

ChemInform ◽  
2012 ◽  
Vol 43 (27) ◽  
pp. no-no
Author(s):  
Daichao Xu ◽  
Chunxin Lu ◽  
Wanzhi Chen
Keyword(s):  
Acetic Acid ◽  
Palladium Catalyzed ◽  
Terminal Olefins

Palladium-catalyzed double arylations of terminal olefins in acetic acid

Tetrahedron ◽  
2012 ◽  
Vol 68 (5) ◽  
pp. 1466-1474 ◽  
Author(s):  
Daichao Xu ◽  
Chunxin Lu ◽  
Wanzhi Chen
Keyword(s):  
Acetic Acid ◽  
Palladium Catalyzed ◽  
Terminal Olefins

scholarly journals Mechanistic investigations of bipyrimidine-promoted palladium-catalyzed allylic acetoxylation of olefins

2009 ◽  
Vol 87 (1) ◽  
pp. 264-271 ◽  
Author(s):  
Bo-Lin Lin ◽  
Jay A Labinger ◽  
John E Bercaw
Keyword(s):  
Acetic Acid ◽  
Key Words ◽  
Palladium Catalysis ◽  
Allylic Oxidation ◽  
Competition Experiment ◽  
Catalyst Precursor ◽  
Mechanistic Studies ◽  
Allyl Acetate ◽  
Palladium Catalyzed ◽  
Terminal Olefins

Several pyridine-like ligands were found to improve Pd(OAc)2-catalyzed allylic oxidation of allylbenzene to cinnamyl acetate by p-benzoquinone in acetic acid. The best ligand examined, bipyrimidine, was used to identify the catalyst precursor for this system, (bipyrimidine)Pd(OAc)2, which was fully characterized. Mechanistic studies suggest the reaction takes place through disproportionation of (bipyrimidine)Pd(OAc)2 to form a bipyrimidine-bridged dimer, which reacts with olefin to form a PdII-olefin adduct, followed by allylic C–H activation to produce (η3-allyl)PdII species. The (η3-allyl)PdII intermediate undergoes a reversible acetate attack to generate a Pd0-(allyl acetate) adduct, which subsequently reacts with p-benzoquinone to release allyl acetate and regenerate (bipyrimidine)Pd(OAc)2. No KIE is observed for the competition experiment between allylbenzene-d0 and allylbenzene-d5 (CD2=CDCD2C6H5), suggesting that allylic C–H activation is not rate-determining. Catalytic allylic acetoxylations of other terminal olefins as well as cyclohexene were also effected by (bipyrimidine)Pd(OAc)2.Key words: olefin, palladium catalysis, allylic C–H oxidation, p-benzoquinone, bipyrimidine.

A Palladium-Catalyzed Dehydrogenative Diamination of Terminal Olefins

2008 ◽  
Vol 120 (43) ◽  
pp. 8348-8351 ◽  
Author(s):  
Bin Wang ◽  
Haifeng Du ◽  
Yian Shi
Keyword(s):  
Palladium Catalyzed ◽  
Terminal Olefins

One-step conversion of isatins to oxindoles and phthalonimides to homophthalimides

1969 ◽  
Vol 47 (5) ◽  
pp. 857-859 ◽  
Author(s):  
J. M. Muchowski
Keyword(s):  
Acetic Acid ◽  
Perchloric Acid ◽  
Palladium Catalyzed ◽  
One Step

The palladium-catalyzed hydrogenation of isatins and phthalonimides in acetic acid containing perchloric acid produced oxindoles and homophthalimides directly.A general, one-step synthesis of phthalonimides from isocarbostyrils is described.

Formation of Bicyclic Cyclopentenone Derivatives by Robinson-Type Annulation of Cyclic β-Oxoesters Containing a 1,4-Diketone Moiety

Synthesis ◽  
2017 ◽  
Vol 49 (17) ◽  
pp. 3874-3884 ◽  
Author(s):  
Irina Geibel ◽  
Christoph Kahrs ◽  
Jens Christoffers
Keyword(s):  
Acetic Acid ◽  
Oxidative Coupling ◽  
Medicinal Chemistry ◽  
Pyridine Derivative ◽  
Reaction Conditions ◽  
Basic Reaction ◽  
Palladium Catalyzed ◽  
Ester Moiety ◽  
Almost All ◽  
Isopropenyl Acetate

Robinson-type cyclopentannulations of cyclic β-oxoesters possessing a 1,4-diketone moiety are accomplished under four different Brønsted basic reaction conditions. Using pyrrolidine/acetic acid in DMSO, an oxohexahydrocyclopenta[a]indene (42%) and an N-Boc-protected oxohexahydrocyclopenta[c]pyridine derivative (62%) are obtained with retention of the ester moieties. The latter compound defines an interesting new scaffold for medicinal chemistry with three positions allowing further derivatizations. The use of KOtBu in DMSO or NaH in toluene leads to cyclopentene derivatives with either partial ester saponification and decarboxylation or displacement of the ester moiety within the carbon skeleton. With aqueous KOH, the cyclopentannulations are successful in almost all cases, but with the ester moieties cleaved off. The respective bicyclic and tricyclic products are obtained in good to excellent yields. The 1,4-diketone starting materials are prepared by cerium-catalyzed oxidative coupling of β-oxoesters with isopropenyl acetate. Alternatively, a two-step sequence consisting of α-propargylation followed by palladium-catalyzed alkyne hydration is used.

scholarly journals Preparation of Allyl and Vinyl Silanes by the Palladium-Catalyzed Silylation of Terminal Olefins: A Silyl-Heck Reaction

2012 ◽  
Vol 51 (15) ◽  
pp. 3663-3667 ◽  
Author(s):  
Jesse R. McAtee ◽  
Sara E. S. Martin ◽  
Derek T. Ahneman ◽  
Keywan A. Johnson ◽  
Donald A. Watson
Keyword(s):  
Heck Reaction ◽  
Palladium Catalyzed ◽  
Vinyl Silanes ◽  
Terminal Olefins
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