Literature DB >> 20607773

Selectivity in metal-catalyzed carbon-carbon bond cleavage of alkylidenecyclopropanes.

Ahmad Masarwa1, Ilan Marek.   

Abstract

When more complex system leads to simpler reactivity profile; the ring-opening of strained three-membered rings such as methylene- and alkylidenecyclopropanes generally lead to several products. If one starts with more functionalized carbon skeletons, selective reactions are now observed and rationalization as well as synthetic applications are described in this concept article. This methodology could be used to the preparation of challenging structural motifs possessing quaternary carbon stereocenters in acyclic systems.

Entities:  

Year:  2010        PMID: 20607773     DOI: 10.1002/chem.201001246

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  15 in total

1.  Merging allylic carbon-hydrogen and selective carbon-carbon bond activation.

Authors:  Ahmad Masarwa; Dorian Didier; Tamar Zabrodski; Marvin Schinkel; Lutz Ackermann; Ilan Marek
Journal:  Nature       Date:  2013-12-08       Impact factor: 49.962

2.  Gold(i)-catalyzed addition of aldehydes to cyclopropylidene bearing 6-aryl-1,5-enynes.

Authors:  Christina A Roselli; Michel R Gagné
Journal:  Org Biomol Chem       Date:  2016-11-29       Impact factor: 3.876

3.  Reductive Decarboxylative Alkynylation of N-Hydroxyphthalimide Esters with Bromoalkynes.

Authors:  Liangbin Huang; Astrid M Olivares; Daniel J Weix
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-17       Impact factor: 15.336

4.  Axial preferences in allylations via the Zimmerman-Traxler transition state.

Authors:  Noga Gilboa; Hao Wang; Kendall N Houk; Ilan Marek
Journal:  Chemistry       Date:  2011-06-03       Impact factor: 5.236

5.  Mechanism and selectivity in nickel-catalyzed cross-electrophile coupling of aryl halides with alkyl halides.

Authors:  Soumik Biswas; Daniel J Weix
Journal:  J Am Chem Soc       Date:  2013-10-21       Impact factor: 15.419

6.  Enantioselective Palladium-Catalyzed Alkenylation of Trisubstituted Alkenols To Form Allylic Quaternary Centers.

Authors:  Harshkumar H Patel; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2016-10-25       Impact factor: 15.419

7.  Cu-Catalyzed Hydroboration of Benzylidenecyclopropanes: Reaction Optimization, (Hetero)Aryl Scope, and Origins of Pathway Selectivity.

Authors:  Jose M Medina; Taeho Kang; Tuğçe G Erbay; Huiling Shao; Gary M Gallego; Shouliang Yang; Michelle Tran-Dubé; Paul F Richardson; Joseph Derosa; Ryan T Helsel; Ryan L Patman; Fen Wang; Christopher P Ashcroft; John F Braganza; Indrawan McAlpine; Peng Liu; Keary M Engle
Journal:  ACS Catal       Date:  2019-10-29       Impact factor: 13.084

Review 8.  Metal-Free Catalysis in C-C Single-Bond Cleavage: Achievements and Prospects.

Authors:  Mohit L Deb; B Shriya Saikia; Iftakur Rahman; Pranjal Kumar Baruah
Journal:  Top Curr Chem (Cham)       Date:  2022-08-11

9.  Fragment Couplings via CO2 Extrusion-Recombination: Expansion of a Classic Bond-Forming Strategy via Metallaphotoredox.

Authors:  Chi Chip Le; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2015-09-15       Impact factor: 15.419

Review 10.  Copper mediated carbometalation reactions.

Authors:  D S Müller; I Marek
Journal:  Chem Soc Rev       Date:  2016-08-08       Impact factor: 54.564

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