Literature DB >> 23627729

The design, synthesis and validation of recoverable and readily reusable siloxane transfer agents for Pd-catalyzed cross-coupling reactions.

Dionicio Martinez-Solorio1, Adam T Hoye, Minh H Nguyen, Amos B Smith.   

Abstract

The development of competent, recoverable and reusable 1-oxa-2-silacyclopentene (siloxane) transfer agents for Pd-catalyzed cross-coupling reactions (CCRs) of organolithium reagents with aryl and alkenyl iodides has been achieved. Drawbacks of the first-generation siloxane-transfer agent (1), relating to facile recovery for potential recycling, have been addressed.

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Year:  2013        PMID： 23627729      PMCID： PMC3762947          DOI： 10.1021/ol400922j

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


  18 in total

Review 1.  Design and implementation of new, silicon-based, cross-coupling reactions: importance of silicon-oxygen bonds.

Authors:  Scott E Denmark; Ramzi F Sweis
Journal:  Acc Chem Res       Date:  2002-10       Impact factor: 22.384

2.  Cross-coupling reactions through the intramolecular activation of alkyl(triorgano)silanes.

Authors:  Yoshiaki Nakao; Masahide Takeda; Takuya Matsumoto; Tamejiro Hiyama
Journal:  Angew Chem Int Ed Engl       Date:  2010-06-14       Impact factor: 15.336

3.  Iridium-catalyzed arene ortho-silylation by formal hydroxyl-directed C-H activation.

Authors:  Eric M Simmons; John F Hartwig
Journal:  J Am Chem Soc       Date:  2010-11-15       Impact factor: 15.419

4.  Silicon-based cross-coupling reaction: an environmentally benign version.

Authors:  Yoshiaki Nakao; Tamejiro Hiyama
Journal:  Chem Soc Rev       Date:  2011-07-14       Impact factor: 54.564

5.  Palladium-catalyzed cross-coupling: a historical contextual perspective to the 2010 Nobel Prize.

Authors:  Carin C C Johansson Seechurn; Matthew O Kitching; Thomas J Colacot; Victor Snieckus
Journal:  Angew Chem Int Ed Engl       Date:  2012-05-09       Impact factor: 15.336

6.  Nickel-catalysed cross-coupling reaction of aryl(trialkyl)silanes with aryl chlorides and tosylates.

Authors:  Shi Tang; Masahide Takeda; Yoshiaki Nakao; Tamejiro Hiyama
Journal:  Chem Commun (Camb)       Date:  2010-08-23       Impact factor: 6.222

7.  Highly stereospecific, palladium-catalyzed cross-coupling of alkenylsilanols

Authors: 
Journal:  Org Lett       Date:  2000-02-24       Impact factor: 6.005

8.  Copper(I) tert-butoxide-promoted 1,4 C(sp(2))-to-O silyl migration: stereospecific allylation of (Z)-gamma-trimethylsilyl allylic alcohols.

Authors:  H Taguchi; K Ghoroku; M Tadaki; A Tsubouchi; T Takeda
Journal:  Org Lett       Date:  2001-11-15       Impact factor: 6.005

9.  Cross-coupling reactions of alkenylsilanolates. Investigation of the mechanism and identification of key intermediates through kinetic analysis.

Authors:  Scott E Denmark; Ramzi F Sweis
Journal:  J Am Chem Soc       Date:  2004-04-21       Impact factor: 15.419

10.  Copper(I) tert-butoxide-promoted 1,4 C sp 2-to-O silyl migration: generation of vinyl copper equivalents and their stereospecific cross-coupling with allylic, aryl, and vinylic halides.

Authors:  Haruhiko Taguchi; Kazushi Ghoroku; Makoto Tadaki; Akira Tsubouchi; Takeshi Takeda
Journal:  J Org Chem       Date:  2002-11-29       Impact factor: 4.354
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  10 in total

Review 1.  Evolution of Anion Relay Chemistry: Construction of Architecturally Complex Natural Products.

Authors:  Yifan Deng; Amos B Smith
Journal:  Acc Chem Res       Date:  2020-04-09       Impact factor: 22.384

2.  Copper-catalyzed electrophilic amination of organolithiums mediated by recoverable siloxane transfer agents.

Authors:  Minh H Nguyen; Amos B Smith
Journal:  Org Lett       Date:  2013-09-03       Impact factor: 6.005

3.  Polymer-supported siloxane transfer agents for Pd-catalyzed cross-coupling reactions.

Authors:  Minh H Nguyen; Amos B Smith
Journal:  Org Lett       Date:  2013-07-31       Impact factor: 6.005

4.  Design, Synthesis, and Application of Polymer-Supported Silicon-Transfer Agents for Cross-Coupling Reactions with Organolithium Reagents.

Authors:  Minh H Nguyen; Kevin T O'Brien; Amos B Smith
Journal:  J Org Chem       Date:  2017-10-02       Impact factor: 4.354

Review 5.  Total synthesis of architecturally complex indole terpenoids: strategic and tactical evolution.

Authors:  Yike Zou; Amos B Smith
Journal:  J Antibiot (Tokyo)       Date:  2017-08-30       Impact factor: 2.649

6.  Synthetic Access to the Mandelalide Family of Macrolides: Development of an Anion Relay Chemistry Strategy.

Authors:  Minh H Nguyen; Masashi Imanishi; Taichi Kurogi; Xuemei Wan; Jane E Ishmael; Kerry L McPhail; Amos B Smith
Journal:  J Org Chem       Date:  2018-02-26       Impact factor: 4.354

7.  Design, Synthesis, and Validation of an Effective, Reusable Silicon-Based Transfer Agent for Room-Temperature Pd-Catalyzed Cross-Coupling Reactions of Aryl and Heteroaryl Chlorides with Readily Available Aryl Lithium Reagents.

Authors:  Dionicio Martinez-Solorio; Bruno Melillo; Luis Sanchez; Yong Liang; Erwin Lam; K N Houk; Amos B Smith
Journal:  J Am Chem Soc       Date:  2016-02-02       Impact factor: 15.419

8.  The role of CuI in the siloxane-mediated Pd-catalyzed cross-coupling reactions of aryl iodides with aryl lithium reagents.

Authors:  Yu Chen; Xiao Zhang; Fang Liu; Gucheng He; Ju Zhang; K N Houk; Amos B Smith; Yong Liang
Journal:  Chin Chem Lett       Date:  2021-01       Impact factor: 6.779

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.  Recyclable polystyrene-supported siloxane-transfer agent for palladium-catalyzed cross-coupling reactions.

Authors:  Minh H Nguyen; Amos B Smith
Journal:  Org Lett       Date:  2014-03-24       Impact factor: 6.005
  10 in total

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