Literature DB >> 24553599

Functional group directed C-H borylation.

A Ros1, R Fernández, J M Lassaletta.   

Abstract

The direct borylation of hydrocarbons via C-H activation has reached an impressive level of sophistication and efficiency, emerging as a fundamental tool in synthesis because of the versatility offered by organoboron compounds. As a remarkable particularity, the catalytic systems originally developed for these reactions are relatively insensitive to directing effects, and the regioselectivity of the borylations is typically governed by steric factors. Likely stimulated by the great synthetic potential of the expected functionalised organoboranes, however, many groups have recently focused on the development of complementary strategies for directed, site-selective borylation reactions where a directing group controls the course of the reaction. In this tutorial review, the different strategies and findings related to the development of these directed borylation reactions via C(sp(2))-H or C(sp(3))-H activation will be summarized and discussed.

Entities:  

Year:  2014        PMID: 24553599     DOI: 10.1039/c3cs60418g

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


  49 in total

1.  Arylphosphonate-Directed Ortho C-H Borylation: Rapid Entry into Highly-Substituted Phosphoarenes.

Authors:  Feiyang Xu; Olivia M Duke; Daniel Rojas; Hanka M Eichelberger; Raphael S Kim; Timothy B Clark; Donald A Watson
Journal:  J Am Chem Soc       Date:  2020-07-02       Impact factor: 15.419

2.  Enantioselective Borylation of Aromatic C-H Bonds with Chiral Dinitrogen Ligands.

Authors:  Bo Su; Tai-Gang Zhou; Pei-Lin Xu; Zhang-Jie Shi; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2017-05-16       Impact factor: 15.336

3.  Cobalt Pincer Complexes in Catalytic C-H Borylation: The Pincer Ligand Flips Rather Than Dearomatizes.

Authors:  Haixia Li; Jennifer V Obligacion; Paul J Chirik; Michael B Hall
Journal:  ACS Catal       Date:  2018-10-17       Impact factor: 13.084

4.  Iridium-Catalyzed Silylation of Five-Membered Heteroarenes: High Sterically Derived Selectivity from a Pyridyl-Imidazoline Ligand.

Authors:  Caleb Karmel; Camille Z Rubel; Elena V Kharitonova; John F Hartwig
Journal:  Angew Chem Weinheim Bergstr Ger       Date:  2020-01-22

5.  Ir-Catalyzed ortho-Borylation of Phenols Directed by Substrate-Ligand Electrostatic Interactions: A Combined Experimental/in Silico Strategy for Optimizing Weak Interactions.

Authors:  Buddhadeb Chattopadhyay; Jonathan E Dannatt; Ivonne L Andujar-De Sanctis; Kristin A Gore; Robert E Maleczka; Daniel A Singleton; Milton R Smith
Journal:  J Am Chem Soc       Date:  2017-05-31       Impact factor: 15.419

6.  Achieving High Ortho Selectivity in Aniline C-H Borylations by Modifying Boron Substituents.

Authors:  Milton R Smith; Ranjana Bisht; Chabush Haldar; Gajanan Pandey; Jonathan E Dannatt; Behnaz Ghaffari; Robert E Maleczka; Buddhadeb Chattopadhyay
Journal:  ACS Catal       Date:  2018-05-09       Impact factor: 13.084

7.  C(sp2)-H Borylation of Heterocycles by Well-Defined Bis(silylene)pyridine Cobalt(III) Precatalysts: Pincer Modification, C(sp2)-H Activation and Catalytically Relevant Intermediates.

Authors:  Rebeca Arevalo; Tyler P Pabst; Paul J Chirik
Journal:  Organometallics       Date:  2020-07-08       Impact factor: 3.876

8.  Iridium-Catalyzed, Hydrosilyl-Directed Borylation of Unactivated Alkyl C-H Bonds.

Authors:  Matthew A Larsen; Seung Hwan Cho; John Hartwig
Journal:  J Am Chem Soc       Date:  2016-01-15       Impact factor: 15.419

9.  Iridium-Catalyzed, Silyl-Directed, peri-Borylation of C-H Bonds in Fused Polycyclic Arenes and Heteroarenes.

Authors:  Bo Su; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2018-07-13       Impact factor: 15.336

Review 10.  A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.

Authors:  Carlo Sambiagio; David Schönbauer; Remi Blieck; Toan Dao-Huy; Gerit Pototschnig; Patricia Schaaf; Thomas Wiesinger; Muhammad Farooq Zia; Joanna Wencel-Delord; Tatiana Besset; Bert U W Maes; Michael Schnürch
Journal:  Chem Soc Rev       Date:  2018-08-28       Impact factor: 54.564

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