Literature DB >> 12379136

Design and implementation of new, silicon-based, cross-coupling reactions: importance of silicon-oxygen bonds.

Scott E Denmark1, Ramzi F Sweis.   

Abstract

This Account chronicles the conceptual development, proof of principle, exploration of scope, and mechanistic investigations of a newly developed class of palladium-catalyzed cross-coupling reactions of silicon derivatives. Under the influence of fluoride activation a myriad of oxygen-containing silicon moieties undergo mild and stereospecific cross-coupling. The diversity of methods for introduction of silicon groupings into organic molecules and the range of organic electrophiles that can be used are outlined.

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Year:  2002        PMID: 12379136     DOI: 10.1021/ar020001r

Source DB:  PubMed          Journal:  Acc Chem Res        ISSN: 0001-4842            Impact factor:   22.384


  43 in total

1.  Direct Hiyama cross-coupling of enaminones with triethoxy(aryl)silanes and dimethylphenylsilanol.

Authors:  Lei Bi; Gunda I Georg
Journal:  Org Lett       Date:  2011-09-22       Impact factor: 6.005

2.  Cross-Coupling Reactions of Alkenylsilanols with Fluoroalkylsulfonates: Development and Optimization of a Mild and Stereospecific Coupling Process.

Authors:  Scott E Denmark; Christopher S Regens
Journal:  Tetrahedron Lett       Date:  2011-04-27       Impact factor: 2.415

3.  Why You Really Should Consider Using Palladium-Catalyzed Cross-Coupling of Silanols and Silanolates.

Authors:  Scott E Denmark; Andrea Ambrosi
Journal:  Org Process Res Dev       Date:  2015       Impact factor: 3.317

4.  Preparation of 2,3-Disubstituted Indoles by Sequential Larock Heteroannulation and Silicon-Based Cross-Coupling Reactions.

Authors:  Scott E Denmark; John D Baird
Journal:  Tetrahedron       Date:  2009-04-18       Impact factor: 2.457

5.  Ligand-enabled cross-coupling of C(sp(3))-H bonds with arylsilanes.

Authors:  Jian He; Ryosuke Takise; Haiyan Fu; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2015-04-02       Impact factor: 15.419

6.  Gold-catalyzed intramolecular allylation of silyl alkynes induced by silane alcoholysis.

Authors:  Sangho Park; Daesung Lee
Journal:  J Am Chem Soc       Date:  2006-08-23       Impact factor: 15.419

7.  Cross-coupling of aromatic bromides with allylic silanolate salts.

Authors:  Scott E Denmark; Nathan S Werner
Journal:  J Am Chem Soc       Date:  2008-12-03       Impact factor: 15.419

8.  Palladium-catalyzed cross-coupling of five-membered heterocyclic silanolates.

Authors:  Scott E Denmark; John D Baird; Christopher S Regens
Journal:  J Org Chem       Date:  2008-01-19       Impact factor: 4.354

9.  Synthetic and mechanistic studies of Pd-catalyzed C-H arylation with diaryliodonium salts: evidence for a bimetallic high oxidation state Pd intermediate.

Authors:  Nicholas R Deprez; Melanie S Sanford
Journal:  J Am Chem Soc       Date:  2009-08-12       Impact factor: 15.419

10.  The interplay of invention, discovery, development, and application in organic synthetic methodology: a case study.

Authors:  Scott E Denmark
Journal:  J Org Chem       Date:  2009-04-17       Impact factor: 4.354

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