A general and efficient catalyst system for a wacker-type oxidation using TBHP as the terminal oxidant: Application to classically challenging substrates

Journal of the American Chemical Society

Volumn 131, Issue 17, 2009, Pages 6076-6077

  Michel, Brian W ^a   Camelio, Andrew M ^a   Cornell, Candace N ^a   Sigman, Matthew S ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLIC ALCOHOL; CATALYTIC SYSTEM; EFFICIENT CATALYSTS; ENANTIOMERIC EXCESS; METHYL KETONES; REDUCED CATALYSTS; SHORT REACTION TIME; TERMINAL OLEFINS; TERMINAL OXIDANTS; WACKER-TYPE OXIDATION;

CATALYSIS; CATALYSTS; KETONES; OLEFINS; OXIDATION; SYNTHESIS (CHEMICAL);

SUBSTRATES;

ACETONE; ALCOHOL DERIVATIVE; ALKENE DERIVATIVE; LIGAND; OXIDIZING AGENT; QUINOLINE 2 OXAZOLINE; QUINOLINE DERIVATIVE; TERT BUTYL HYDROPEROXIDE; UNCLASSIFIED DRUG; ALKENE; KETONE; PALLADIUM;

ALLYLATION; AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CATALYST; ENANTIOMER; ENANTIOSELECTIVITY; OXIDATION; OXIDATION REDUCTION REACTION; REACTION TIME; SYNTHESIS; WACKER OXIDATION; CHEMICAL STRUCTURE; CHEMISTRY;

ALKENES; CATALYSIS; KETONES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PALLADIUM; TERT-BUTYLHYDROPEROXIDE;

EID: 70149083698     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja901212h     Document Type: Article

References (18)

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17. 6 > OTf ̃ BF4.
18. As per reviewer suggestion, we have submitted a hindered terminal alkene, 1-ethenyladamantane, to our reaction conditions yielding (94% by GC in 15 min) only the methyl ketone product as determined by GC and 1H NMR. (12) The aldehyde product is the result of oxidative cleavage of the alkene. (13) See Supporting Information for details.