Literature DB >> 25782140

Iron-catalyzed C-H borylation of arenes.

Thomas Dombray1, C Gunnar Werncke2,3, Shi Jiang1, Mary Grellier2,3, Laure Vendier2,3, Sébastien Bontemps2,3, Jean-Baptiste Sortais1, Sylviane Sabo-Etienne2,3, Christophe Darcel1.   

Abstract

Well-defined iron bis(diphosphine) complexes are active catalysts for the dehydrogenative C-H borylation of aromatic and heteroaromatic derivatives with pinacolborane. The corresponding borylated compounds were isolated in moderate to good yields (25-73%) with a 5 mol% catalyst loading under UV irradiation (350 nm) at room temperature. Stoichiometric reactivity studies and isolation of an original trans-hydrido(boryl)iron complex, Fe(H)(Bpin)(dmpe)2, allowed us to propose a mechanism showing the role of some key catalytic species.

Entities:  

Year:  2015        PMID: 25782140     DOI: 10.1021/jacs.5b00895

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  15 in total

1.  Reversible Borylene Formation from Ring Opening of Pinacolborane and Other Intermediates Generated from Five-Coordinate Tris-Boryl Complexes: Implications for Catalytic C-H Borylation.

Authors:  Behnaz Ghaffari; Britt A Vanchura; Ghayoor A Chotana; Richard J Staples; Daniel Holmes; Robert E Maleczka; Milton R Smith
Journal:  Organometallics       Date:  2015-08-11       Impact factor: 3.876

2.  Benzyltriboronates: Building Blocks for Diastereoselective Carbon-Carbon Bond Formation.

Authors:  W Neil Palmer; Cayetana Zarate; Paul J Chirik
Journal:  J Am Chem Soc       Date:  2017-02-13       Impact factor: 15.419

3.  Enabling Two-Electron Pathways with Iron and Cobalt: From Ligand Design to Catalytic Applications.

Authors:  Rebeca Arevalo; Paul J Chirik
Journal:  J Am Chem Soc       Date:  2019-05-28       Impact factor: 15.419

4.  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

5.  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

Review 6.  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

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.  Ligand-Promoted Borylation of C(sp(3))-H Bonds with Palladium(II) Catalysts.

Authors:  Jian He; Heng Jiang; Ryosuke Takise; Ru-Yi Zhu; Gang Chen; Hui-Xiong Dai; T G Murali Dhar; Jun Shi; Hao Zhang; Peter T W Cheng; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2015-11-27       Impact factor: 15.336

9.  Insights into Activation of Cobalt Pre-Catalysts for C(sp2)-H Functionalization.

Authors:  Jennifer V Obligacion; Hongyu Zhong; Paul J Chirik
Journal:  Isr J Chem       Date:  2017-09-25       Impact factor: 3.333

10.  Mechanistic Studies of Cobalt-Catalyzed C(sp2)-H Borylation of Five-Membered Heteroarenes with Pinacolborane.

Authors:  Jennifer V Obligacion; Paul J Chirik
Journal:  ACS Catal       Date:  2017-05-17       Impact factor: 13.084

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