Literature DB >> 26892551

Remote functionalization through alkene isomerization.

Alexandre Vasseur1, Jeffrey Bruffaerts1, Ilan Marek1.   

Abstract

Exploiting the reactivity of one functional group within a molecule to generate a reaction at a different position is an ongoing challenge in organic synthesis. Effective remote functionalization protocols have the potential to provide access to almost any derivatives but are difficult to achieve. The difficulty is more pronounced for acyclic systems where flexible alkyl chains are present between the initiating functional group and the desired reactive centres. In this Review, we discuss the concept of remote functionalization of alkenes using metal complexes, leading to a selective reaction at a position distal to the initial double bond. We aim to show the vast opportunity provided by this growing field through selected and representative examples. Our aim is to demonstrate that using a double bond as a chemical handle, metal-assisted long-distance activation could be used as a powerful synthetic strategy.

Entities:  

Year:  2016        PMID: 26892551     DOI: 10.1038/nchem.2445

Source DB:  PubMed          Journal:  Nat Chem        ISSN: 1755-4330            Impact factor:   24.427


  45 in total

1.  Enantioselective synthesis of anti homoallylic alcohols from terminal alkynes and aldehydes based on concomitant use of a cationic iridium complex and a chiral phosphoric acid.

Authors:  Tomoya Miura; Yui Nishida; Masao Morimoto; Masahiro Murakami
Journal:  J Am Chem Soc       Date:  2013-07-30       Impact factor: 15.419

2.  Simple Amine-Directed Meta-Selective C-H Arylation via Pd/Norbornene Catalysis.

Authors:  Zhe Dong; Jianchun Wang; Guangbin Dong
Journal:  J Am Chem Soc       Date:  2015-04-28       Impact factor: 15.419

3.  Palladium-catalyzed enantioselective Heck alkenylation of acyclic alkenols using a redox-relay strategy.

Authors:  Harshkumar H Patel; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2015-03-09       Impact factor: 15.419

4.  Bis(imino)pyridine cobalt-catalyzed alkene isomerization-hydroboration: a strategy for remote hydrofunctionalization with terminal selectivity.

Authors:  Jennifer V Obligacion; Paul J Chirik
Journal:  J Am Chem Soc       Date:  2013-12-16       Impact factor: 15.419

5.  Dramatic effect of Lewis acids on the rhodium-catalyzed hydroboration of olefins.

Authors:  Christopher J Lata; Cathleen M Crudden
Journal:  J Am Chem Soc       Date:  2010-01-13       Impact factor: 15.419

6.  Ligand-enabled meta-C-H activation using a transient mediator.

Authors:  Xiao-Chen Wang; Wei Gong; Li-Zhen Fang; Ru-Yi Zhu; Suhua Li; Keary M Engle; Jin-Quan Yu
Journal:  Nature       Date:  2015-03-09       Impact factor: 49.962

7.  Linear-selective hydroarylation of unactivated terminal and internal olefins with trifluoromethyl-substituted arenes.

Authors:  Joseph S Bair; York Schramm; Alexey G Sergeev; Eric Clot; Odile Eisenstein; John F Hartwig
Journal:  J Am Chem Soc       Date:  2014-09-15       Impact factor: 15.419

8.  Ruthenium-catalyzed hydroformylation/reduction of olefins to alcohols: extending the scope to internal alkenes.

Authors:  Lipeng Wu; Ivana Fleischer; Ralf Jackstell; Irina Profir; Robert Franke; Matthias Beller
Journal:  J Am Chem Soc       Date:  2013-09-17       Impact factor: 15.419

9.  Mechanism, reactivity, and selectivity in palladium-catalyzed redox-relay Heck arylations of alkenyl alcohols.

Authors:  Liping Xu; Margaret J Hilton; Xinhao Zhang; Per-Ola Norrby; Yun-Dong Wu; Matthew S Sigman; Olaf Wiest
Journal:  J Am Chem Soc       Date:  2014-01-22       Impact factor: 15.419

10.  Conformation-induced remote meta-C-H activation of amines.

Authors:  Ri-Yuan Tang; Gang Li; Jin-Quan Yu
Journal:  Nature       Date:  2014-03-13       Impact factor: 49.962

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  49 in total

1.  Remote carboxylation of halogenated aliphatic hydrocarbons with carbon dioxide.

Authors:  Francisco Juliá-Hernández; Toni Moragas; Josep Cornella; Ruben Martin
Journal:  Nature       Date:  2017-05-03       Impact factor: 49.962

2.  Organic chemistry: Nickel steps towards selectivity.

Authors:  Matthew Gaunt; Patrick Williamson
Journal:  Nature       Date:  2017-05-03       Impact factor: 49.962

3.  Practically simple reactions convert hydrocarbons to precious chemicals.

Authors:  James P Morken
Journal:  Nature       Date:  2018-11       Impact factor: 49.962

4.  Aza-Heterocycles via Copper-Catalyzed, Remote C-H Desaturation of Amines.

Authors:  Leah M Stateman; Ross M Dare; Alyson N Paneque; David A Nagib
Journal:  Chem       Date:  2021-11-16       Impact factor: 22.804

5.  Development and Mechanistic Interrogation of Interrupted Chain-Walking in the Enantioselective Relay Heck Reaction.

Authors:  Sean P Ross; Ajara A Rahman; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2020-05-29       Impact factor: 15.419

6.  Catalytic enantioselective arylative cyclizations of alkynyl 1,3-diketones by 1,4-rhodium(i) migration.

Authors:  Alistair Groves; Jinwei Sun; Hal R I Parke; Michael Callingham; Stephen P Argent; Laurence J Taylor; Hon Wai Lam
Journal:  Chem Sci       Date:  2020-02-06       Impact factor: 9.825

7.  Enantioselective access to chiral aliphatic amines and alcohols via Ni-catalyzed hydroalkylations.

Authors:  Shan Wang; Jian-Xin Zhang; Tian-Yi Zhang; Huan Meng; Bi-Hong Chen; Wei Shu
Journal:  Nat Commun       Date:  2021-05-13       Impact factor: 14.919

8.  Mechanistic Studies of Pd(II)-Catalyzed E/Z Isomerization of Unactivated Alkenes: Evidence for a Monometallic Nucleopalladation Pathway.

Authors:  Rei Matsuura; Malkanthi K Karunananda; Mingyu Liu; Nhi Nguyen; Donna G Blackmond; Keary M Engle
Journal:  ACS Catal       Date:  2021-03-19       Impact factor: 13.084

9.  Ru-catalyzed isomerization of ω-alkenylboronates towards stereoselective synthesis of vinylboronates with subsequent in situ functionalization.

Authors:  Guo-Ming Ho; Lucas Segura; Ilan Marek
Journal:  Chem Sci       Date:  2020-05-26       Impact factor: 9.825

10.  Stereoselective tandem iridium-catalyzed alkene isomerization-cope rearrangement of ω-diene epoxides: efficient access to acyclic 1,6-dicarbonyl compounds.

Authors:  Rahul Suresh; Itai Massad; Ilan Marek
Journal:  Chem Sci       Date:  2021-06-09       Impact factor: 9.825

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