Literature DB >> 20838677

Recent advances in the use of temporary silicon tethers in metal-mediated reactions.

Sonia Bracegirdle1, Edward A Anderson.   

Abstract

This tutorial review describes the use of temporary silicon tethers in metal-mediated organic reactions, a strategy which although well-established in traditional organic synthesis is still a blossoming field in the organometallic arena. The benefits of silicon-tethering are manifold: the reactivity, selectivity, and efficiency of organometallic processes can all be dramatically enhanced, often with unique regio- and stereochemical outcomes compared to the analogous intermolecular transformations. In addition, the residual silicon functionality can undergo a wide range of chemistry subsequent to the tethered reaction, creating further synthetic opportunities.

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Year:  2010        PMID: 20838677     DOI: 10.1039/c0cs00007h

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  14 in total

1.  Silicon-Tethered Strategies for C-H Functionalization Reactions.

Authors:  Marvin Parasram; Vladimir Gevorgyan
Journal:  Acc Chem Res       Date:  2017-08-03       Impact factor: 22.384

2.  Reverse cope elimination of hydroxylamines and alkenes or alkynes: theoretical investigation of tether length and substituent effects.

Authors:  Elizabeth H Krenske; Edwin C Davison; Ian T Forbes; Jacqueline A Warner; Adrian L Smith; Andrew B Holmes; K N Houk
Journal:  J Am Chem Soc       Date:  2012-01-17       Impact factor: 15.419

3.  Silylation reactions on nanoporous gold via homolytic Si-H activation of silanes.

Authors:  Hongbo Li; Huifang Guo; Zhiwen Li; Cai Wu; Jing Li; Chunliang Zhao; Shuangxi Guo; Yi Ding; Wei He; Yadong Li
Journal:  Chem Sci       Date:  2018-04-30       Impact factor: 9.825

4.  Pd-catalyzed modifiable silanol-directed aromatic C-H oxygenation.

Authors:  Chunhui Huang; Nugzar Ghavtadze; Benhur Godoi; Vladimir Gevorgyan
Journal:  Chemistry       Date:  2012-07-02       Impact factor: 5.236

5.  The Pyridyldiisopropylsilyl Group: A Masked Functionality and Directing Group for Monoselective ortho-Acyloxylation and ortho-Halogenation Reactions of Arenes.

Authors:  Chunhui Huang; Natalia Chernyak; Alexander S Dudnik; Vladimir Gevorgyan
Journal:  Adv Synth Catal       Date:  2011-05-01       Impact factor: 5.837

6.  A catalytic asymmetric synthesis of polysubstituted piperidines using a rhodium(I)-catalyzed [2+2+2] cycloaddition employing a cleavable tether.

Authors:  Timothy J Martin; Tomislav Rovis
Journal:  Angew Chem Int Ed Engl       Date:  2013-04-19       Impact factor: 15.336

7.  Iridium-Catalyzed, Silyl-Directed, peri-Borylation of C-H Bonds in Fused Polycyclic Arenes and Heteroarenes.

Authors:  Bo Su; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2018-07-13       Impact factor: 15.336

8.  Sugar Silanes: Versatile Reagents for Stereocontrolled Glycosylation via Intramolecular Aglycone Delivery.

Authors:  Jordan T Walk; Zachary A Buchan; John Montgomery
Journal:  Chem Sci       Date:  2015-06-01       Impact factor: 9.825

9.  Direct catalytic cross-coupling of alkenyllithium compounds.

Authors:  Valentín Hornillos; Massimo Giannerini; Carlos Vila; Martín Fañanás-Mastral; Ben L Feringa
Journal:  Chem Sci       Date:  2014-11-28       Impact factor: 9.825

10.  Synthesis of cyclic alkenylsiloxanes by semihydrogenation: a stereospecific route to (Z)-alkenyl polyenes.

Authors:  Bryony L Elbert; Diane S W Lim; Haraldur G Gudmundsson; Jack A O'Hanlon; Edward A Anderson
Journal:  Chemistry       Date:  2014-06-04       Impact factor: 5.236

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