Literature DB >> 29071326

Access to the meta position of arenes through transition metal catalysed C-H bond functionalisation: a focus on metals other than palladium.

Madalina T Mihai1, Georgi R Genov, Robert J Phipps.   

Abstract

The elaboration of simple arenes in order to access more complex substitution patterns is a crucial endeavor for synthetic chemists, given the central role that aromatic rings play in all manner of important molecules. Classical methods are now routinely used alongside stoichiometric organometallic approaches and, most recently, transition metal catalysis in the range of methodologies that are available to elaborate arene C-H bonds. Regioselectivity is an important consideration when selecting a method and, of all those available, it is arguably those that target the meta position that are fewest in number. The rapid development of transition metal-catalysed C-H bond functionalisation over the last few decades has opened new possibilities for meta-selective C-H functionalisation through the diverse reactivity of transition metals and their compatibility with a wide range of directing groups. The pace of discovery of such processes has grown rapidly in the last five years in particular and it is the purpose of this review to examine these but in doing so to place the focus on metals other than palladium, the specific contributions of which have been very recently reviewed elsewhere. It is hoped this will serve to highlight to the reader the breadth of current strategies and mechanisms that have been used to tackle this challenge, which may inspire further progress in the field.

Entities:  

Year:  2018        PMID: 29071326     DOI: 10.1039/c7cs00637c

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  16 in total

1.  C-H activation by immobilized heterogeneous photocatalysts.

Authors:  Isaac Choi; Julia Struwe; Lutz Ackermann
Journal:  Photochem Photobiol Sci       Date:  2021-11-16       Impact factor: 3.982

2.  A directive Ni catalyst overrides conventional site selectivity in pyridine C-H alkenylation.

Authors:  Tao Zhang; Yu-Xin Luan; Nelson Y S Lam; Jiang-Fei Li; Yue Li; Mengchun Ye; Jin-Quan Yu
Journal:  Nat Chem       Date:  2021-10-11       Impact factor: 24.427

Review 3.  C-H bond activation and sequential addition to two different coupling partners: a versatile approach to molecular complexity.

Authors:  Daniel S Brandes; Jonathan A Ellman
Journal:  Chem Soc Rev       Date:  2022-08-01       Impact factor: 60.615

4.  Rhodium catalyzed template-assisted distal para-C-H olefination.

Authors:  Uttam Dutta; Sudip Maiti; Sandeep Pimparkar; Siddhartha Maiti; Lawrence R Gahan; Elizabeth H Krenske; David W Lupton; Debabrata Maiti
Journal:  Chem Sci       Date:  2019-06-21       Impact factor: 9.825

5.  Ion-Pair-Directed Borylation of Aromatic Phosphonium Salts.

Authors:  Bernadette Lee; Madalina T Mihai; Violeta Stojalnikova; Robert J Phipps
Journal:  J Org Chem       Date:  2019-06-04       Impact factor: 4.354

Review 6.  Recent Advances on Synthetic Methodology Merging C-H Functionalization and C-C Cleavage.

Authors:  Hamid Azizollahi; José-Antonio García-López
Journal:  Molecules       Date:  2020-12-13       Impact factor: 4.411

7.  Regiocontrol in the oxidative Heck reaction of indole by ligand-enabled switch of the regioselectivity-determining step.

Authors:  Yu-Jie Wang; Chen-Hui Yuan; De-Zhao Chu; Lei Jiao
Journal:  Chem Sci       Date:  2020-09-23       Impact factor: 9.825

8.  Para-Selective C-H Borylation of Common Arene Building Blocks Enabled by Ion-Pairing with a Bulky Countercation.

Authors:  Madalina T Mihai; Benjamin D Williams; Robert J Phipps
Journal:  J Am Chem Soc       Date:  2019-09-18       Impact factor: 15.419

9.  One-Pot Iridium Catalyzed C-H Borylation/Sonogashira Cross-Coupling: Access to Borylated Aryl Alkynes.

Authors:  Ghayoor A Chotana; Jose R Montero Bastidas; Susanne L Miller; Milton R Smith; Robert E Maleczka
Journal:  Molecules       Date:  2020-04-10       Impact factor: 4.411

10.  Regiodivergent C-H and Decarboxylative C-C Alkylation by Ruthenium Catalysis: ortho versus meta Position-Selectivity.

Authors:  Korkit Korvorapun; Marc Moselage; Julia Struwe; Torben Rogge; Antonis M Messinis; Lutz Ackermann
Journal:  Angew Chem Int Ed Engl       Date:  2020-08-25       Impact factor: 16.823

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