Literature DB >> 29104453

Heck-like Reactions Involving Heteroatomic Electrophiles.

Bojan Vulovic1, Donald A Watson1.   

Abstract

class="Chemical">Siclass="Chemical">nce the discovery of the class="Chemical">n class="Chemical">Heck reaction in the early seventies, this reaction has become a powerful tool in synthetic organic chemistry. By employing heteroatomic instead of traditional carbon electrophiles, the Heck reaction shows an intriguing flexibility. These "hetereoatomic-Heck reactions" reinvigorate the area, offering new routes to highly useful synthetic precursors and structural motifs present in biologically active compounds. This microreview focuses on early developments leading to the heteroatomic-Heck reactions (silyl-Heck, boryl-Heck and intramolecular aza-Heck), current state of the emerging area, as well as that of a few related processes.

Entities:  

Keywords:  Heck-Reaction; aza-Heckl; boryl-Heck; hetereoatomic-Heck; silyl-Heck

Year:  2017        PMID: 29104453      PMCID: PMC5665589          DOI: 10.1002/ejoc.201700485

Source DB:  PubMed          Journal:  European J Org Chem        ISSN: 1099-0690


  33 in total

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Journal:  Angew Chem Int Ed Engl       Date:  2010-04-12       Impact factor: 15.336

2.  Chasing a phantom by total synthesis: the butylcycloheptylprodigiosin case.

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Journal:  Angew Chem Int Ed Engl       Date:  2005-04-29       Impact factor: 15.336

3.  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

4.  The asymmetric Heck and related reactions.

Authors:  Dennis Mc Cartney; Patrick J Guiry
Journal:  Chem Soc Rev       Date:  2011-06-15       Impact factor: 54.564

5.  Preparation of allyl and vinyl silanes by the palladium-catalyzed silylation of terminal olefins: a silyl-Heck reaction.

Authors:  Jesse R McAtee; Sara E S Martin; Derek T Ahneman; Keywan A Johnson; Donald A Watson
Journal:  Angew Chem Int Ed Engl       Date:  2012-03-01       Impact factor: 15.336

6.  Direct Synthesis of Alkenyl Boronic Esters from Unfunctionalized Alkenes: A Boryl-Heck Reaction.

Authors:  William B Reid; Jesse J Spillane; Sarah B Krause; Donald A Watson
Journal:  J Am Chem Soc       Date:  2016-04-22       Impact factor: 15.419

7.  Palladium-catalysed cross-coupling of organosilicon reagents.

Authors:  Hannah F Sore; Warren R J D Galloway; David R Spring
Journal:  Chem Soc Rev       Date:  2011-11-02       Impact factor: 54.564

8.  Palladium catalyzed cyclizations of oxime esters with 1,1-disubstituted alkenes: synthesis of α,α-disubstituted dihydropyrroles and studies towards an asymmetric protocol.

Authors:  Adele Faulkner; James S Scott; John F Bower
Journal:  Chem Commun (Camb)       Date:  2013-02-21       Impact factor: 6.222

9.  Palladium catalyzed cyclizations of oxime esters with 1,2-disubstituted alkenes: synthesis of dihydropyrroles.

Authors:  Nicholas J Race; John F Bower
Journal:  Org Lett       Date:  2013-08-27       Impact factor: 6.005

10.  Some aspects of radical chemistry in the assembly of complex molecular architectures.

Authors:  Béatrice Quiclet-Sire; Samir Z Zard
Journal:  Beilstein J Org Chem       Date:  2013-03-18       Impact factor: 2.883

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  12 in total

Review 1.  Cross-Coupling of Heteroatomic Electrophiles.

Authors:  Katerina M Korch; Donald A Watson
Journal:  Chem Rev       Date:  2019-06-11       Impact factor: 60.622

2.  Stereoselective Synthesis of Cis- and Trans-Tetrasubstituted Vinyl Silanes Using a Silyl-Heck Strategy and Hiyama Conditions for Their Cross-Coupling.

Authors:  Michael F Wisthoff; Sarah B Pawley; Andrew P Cinderella; Donald A Watson
Journal:  J Am Chem Soc       Date:  2020-06-30       Impact factor: 15.419

3.  Synthesis of N-H Bearing Imidazolidinones and Dihydroimidazolones Using Aza-Heck Cyclizations.

Authors:  Feiyang Xu; Scott A Shuler; Donald A Watson
Journal:  Angew Chem Int Ed Engl       Date:  2018-08-19       Impact factor: 15.336

4.  Synthesis of Indolines and Derivatives by Aza-Heck Cyclization.

Authors:  Feiyang Xu; Katerina M Korch; Donald A Watson
Journal:  Angew Chem Int Ed Engl       Date:  2019-08-13       Impact factor: 15.336

Review 5.  Inorganometallics (Transition Metal-Metalloid Complexes) and Catalysis.

Authors:  Bogdan Marciniec; Cezary Pietraszuk; Piotr Pawluć; Hieronim Maciejewski
Journal:  Chem Rev       Date:  2021-12-30       Impact factor: 60.622

6.  Total Synthesis of (±)-Impatien A via Aza-Heck Cyclization.

Authors:  Katerina M Korch; Donald A Watson
Journal:  Org Lett       Date:  2021-08-30       Impact factor: 6.072

7.  Catalytic Asymmetric Intermolecular Allylic Functionalization of Unactivated Internal Alkenes.

Authors:  Liela Bayeh; Uttam K Tambar
Journal:  ACS Catal       Date:  2017-10-27       Impact factor: 13.084

8.  A Bench-Stable, Single-Component Precatalyst for Silyl-Heck Reactions.

Authors:  Sarah B Krause; Jesse R McAtee; Glenn P A Yap; Donald A Watson
Journal:  Org Lett       Date:  2017-09-29       Impact factor: 6.005

9.  Tandem aza-Heck Suzuki and carbonylation reactions of O-phenyl hydroxamic ethers: complex lactams via carboamination.

Authors:  Run-Duo Gao; Scott A Shuler; Donald A Watson
Journal:  Chem Sci       Date:  2021-05-27       Impact factor: 9.825

10.  Synthesis of 1,1-Diboryl Alkenes Using the Boryl-Heck Reaction.

Authors:  Olamide O Idowu; Jacob C Hayes; William B Reid; Donald A Watson
Journal:  Org Lett       Date:  2021-05-27       Impact factor: 6.072

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