Document Detail

Facile Regio- and Stereoselective Hydrometallation of Alkynes with a Combination of Carboxylic Acids and Group 10 Transition Metal Complexes: Selective Hydrogenation of Alkynes with Formic Acid.
MedLine Citation:
PMID:  21916436     Owner:  NLM     Status:  Publisher    
A facile, highly stereo- and regioselective hydrometallation of alkynes generating alkenylmetal complex is disclosed for the first time from a reaction of alkyne, carboxylic acid and a zero valent group 10 transition metal complex M(PEt3)4 (M = Ni, Pd, Pt). A mechanistic study showed that the hydrometallation does not proceed via the reaction of alkyne with a hydridometal generated by the protonation of a carboxylic acid with Pt(PEt3)4, but proceeds via a reaction of an alkyne coordinate metal complex with the acid. This finding clarifies the long proposed reaction mechanism, that operates via the generation of an alkenylpalladium intermediate and subsequent transformation of this complex in a variety of reactions catalyzed by a combination of Brnsted acid and Pd(0) complex. This finding also leads to the disclosure of an unprecedented reduction of alkynes with formic acid that can selectively produce cis-, trans-alkenes and alkanes by slightly tuning the conditions.
Ruwei Shen; Tieqiao Chen; Yalei Zhao; Renhua Qiu; Yongbo Zhou; Shuangfeng Yin; Xiangbo Wang; Midori Goto; Li-Biao Han
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2011-9-14
Journal Detail:
Title:  Journal of the American Chemical Society     Volume:  -     ISSN:  1520-5126     ISO Abbreviation:  -     Publication Date:  2011 Sep 
Date Detail:
Created Date:  2011-9-15     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  7503056     Medline TA:  J Am Chem Soc     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
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