Literature DB >> 16268535

Trans- and cis-selective Lewis acid catalyzed hydrogermylation of alkynes.

Todd Schwier1, Vladimir Gevorgyan.   

Abstract

[reactions: see text] The first examples of Lewis acid catalyzed hydrogermylation of alkynes have been demonstrated. It was found that this method has much higher functional group compatibility compared to the known Lewis acid catalyzed hydrosilylation and hydrostannation reactions. Remarkably, the stereochemical outcome of this hydrogermylation reaction depends on the nature of the alkyne used: proceeding via a trans-addition pathway with simple alkynes and cis-addition with propiolates. Mechanistic studies strongly support the proposed rationale on the origins of cis-selectivity in the hydrogermylation of activated alkynes.

Entities:  

Year:  2005        PMID： 16268535     DOI： 10.1021/ol0521026

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  9 in total

1.  Metal-catalyzed [1,2]-alkyl shift in allenyl ketones: synthesis of multisubstituted furans.

Authors:  Alexander S Dudnik; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

2.  Application of germyldesulfonylation reactions to the synthesis of germanium-containing nucleoside analogues.

Authors:  Stanislaw F Wnuk; Pablo R Sacasa; Jorge Restrepo
Journal:  Nucleosides Nucleotides Nucleic Acids       Date:  2009-05       Impact factor: 1.381

3.  (Z)-(2-bromovinyl)-MIDA boronate: a readily accessible and highly versatile building block for small molecule synthesis.

Authors:  Eric M Woerly; Justin R Struble; Nagarjuna Palyam; Sean P O'Hara; Martin D Burke
Journal:  Tetrahedron       Date:  2011-06-17       Impact factor: 2.457

4.  A simple and general platform for generating stereochemically complex polyene frameworks by iterative cross-coupling.

Authors:  Suk Joong Lee; Thomas M Anderson; Martin D Burke
Journal:  Angew Chem Int Ed Engl       Date:  2010-11-15       Impact factor: 15.336

5.  Anti-selective epoxidation of methyl alpha-methylene-beta-tert-butyldimethylsilyloxycarboxylate esters. Evidence for stereospecific oxygen atom transfer in a nucleophilic epoxidation process.

Authors:  Jakub Svenda; Andrew G Myers
Journal:  Org Lett       Date:  2009-06-04       Impact factor: 6.005

6.  Metal-catalyzed 1,2-shift of diverse migrating groups in allenyl systems as a new paradigm toward densely functionalized heterocycles.

Authors:  Alexander S Dudnik; Anna W Sromek; Marina Rubina; Joseph T Kim; Alexander V Kel'in; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2008-01-04       Impact factor: 15.419

7.  Hydrogermylation of 5-ethynyluracil nucleosides: formation of 5-(2-germylvinyl)uracil and 5-(2-germylacetyl)uracil nucleosides.

Authors:  Yong Liang; Jean-Philippe Pitteloud; Stanislaw F Wnuk
Journal:  J Org Chem       Date:  2013-05-13       Impact factor: 4.354

8.  Palladium-catalyzed transformations of salvinorin A, a neoclerodane diterpene from Salvia divinorum.

Authors:  Andrew P Riley; Victor W Day; Hernán A Navarro; Thomas E Prisinzano
Journal:  Org Lett       Date:  2013-11-18       Impact factor: 6.005

Review 9.  Recent advances in transition metal-free catalytic hydroelementation (E = B, Si, Ge, and Sn) of alkynes.

Authors:  Vitthal B Saptal; Ruibin Wang; Sehoon Park
Journal:  RSC Adv       Date:  2020-12-07       Impact factor: 4.036
  9 in total

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