Document Detail


A new approach to carbon-carbon bond formation: Development of aerobic Pd-catalyzed reductive coupling reactions of organometallic reagents and styrenes.
MedLine Citation:
PMID:  20161306     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
Alkenes are attractive starting materials for organic synthesis and the development of new selective functionalization reactions are desired. Previously, our laboratory discovered a unique Pd-catalyzed hydroalkoxylation reaction of styrenes containing a phenol. Based upon deuterium labeling experiments, a mechanism involving an aerobic alcohol oxidation coupled to alkene functionalization was proposed. These results inspired the development of a new Pd-catalyzed reductive coupling reaction of alkenes and organometallic reagents that generates a new carbon-carbon bond. Optimization of the conditions for the coupling of both organostannanes and organoboronic esters is described and the initial scope of the transformation is presented. Additionally, several mechanistic experiments are outlined and support the rationale for the development of the reaction based upon coupling alcohol oxidation to alkene functionalization.
Authors:
Keith M Gligorich; Yasumasa Iwai; Sarah A Cummings; Matthew S Sigman
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Publication Detail:
Type:  JOURNAL ARTICLE    
Journal Detail:
Title:  Tetrahedron     Volume:  65     ISSN:  0040-4020     ISO Abbreviation:  -     Publication Date:  2009 Jun 
Date Detail:
Created Date:  2010-7-13     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2984170R     Medline TA:  Tetrahedron     Country:  -    
Other Details:
Languages:  ENG     Pagination:  5074-5083     Citation Subset:  -    
Affiliation:
Department of Chemistry, University of Utah, 315 South 1400 East Salt Lake City, UT 84112, USA.
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Descriptor/Qualifier:
Grant Support
ID/Acronym/Agency:
R01 GM063540-06A2//NIGMS NIH HHS; R56 GM063540-06//NIGMS NIH HHS

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