ChemInform Abstract: Synthesis of (.+-.)-10-epi-Elemol by a Highly Stereoselective Intramolecular Palladium-Catalyzed Coupling of an Allylstannane with an Allyl Acetate.

ChemInform ◽  
2010 ◽  
Vol 29 (12) ◽  
pp. no-no
Author(s):  
J. M. CUERVA ◽  
E. GOMEZ-BENGOA ◽  
M. MENDEZ ◽  
A. M. ECHAVARREN
Keyword(s):  
Allyl Acetate ◽  
Palladium Catalyzed

ChemInform Abstract: Palladium-Catalyzed Coupling of Haloalkynes with Allyl Acetate: A Regio- and Stereoselective Synthesis of (Z)-β-Haloenol Acetates.

ChemInform ◽  
2011 ◽  
Vol 42 (49) ◽  
pp. no-no
Author(s):  
Xiaoyi Chen ◽  
Dongxu Chen ◽  
Zenghui Lu ◽  
Lichun Kong ◽  
Gangguo Zhu
Keyword(s):  
Stereoselective Synthesis ◽  
Allyl Acetate ◽  
Palladium Catalyzed

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.

Palladium-catalyzed cross-coupling reaction: Direct allylation of aryl bromides with allyl acetate

1985 ◽  
Vol 26 (52) ◽  
pp. 6457-6460 ◽  
Author(s):  
Yuusaku Yokoyama ◽  
Sadao Ito ◽  
Yumi Takahashi ◽  
Yasuoki Murakami
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Allyl Acetate ◽  
Aryl Bromides ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed

Palladium-Catalyzed Coupling of Haloalkynes with Allyl Acetate: A Regio- and Stereoselective Synthesis of (Z)-β-Haloenol Acetates

2011 ◽  
Vol 76 (15) ◽  
pp. 6338-6343 ◽  
Author(s):  
Xiaoyi Chen ◽  
Dongxu Chen ◽  
Zenghui Lu ◽  
Lichun Kong ◽  
Gangguo Zhu
Keyword(s):  
Stereoselective Synthesis ◽  
Allyl Acetate ◽  
Palladium Catalyzed
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