Literature DB >> 28508564

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

Bo Su1,2, Tai-Gang Zhou1, Pei-Lin Xu1, Zhang-Jie Shi1,3, John F Hartwig2.   

Abstract

The borylation of C-H bonds catalyzed by transition metals has been investigated extensively in the past two decades, but no iridium-catalyzed enantioselective borylation of C-H bonds has been reported. We report a set of iridium-catalyzed enantioselective borylations of aromatic C-H bonds. This reaction relies on a set of newly developed chiral quinolyl oxazoline ligands. This process proceeds under mild conditions with good to excellent enantioselectivity, and the borylated products can be converted to enantioenriched derivatives containing new C-O, C-C, C-Cl, or C-Br bonds.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−H activation; asymmetric catalysis; borylation; chiral dinitrogen ligand; iridium

Mesh:

Substances:

Year:  2017        PMID: 28508564      PMCID: PMC5852249          DOI: 10.1002/anie.201702628

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  50 in total

1.  Pd-catalyzed oxidative ortho-C-H borylation of arenes.

Authors:  Hui-Xiong Dai; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2011-12-19       Impact factor: 15.419

2.  Rhodium-catalyzed enantioselective intramolecular C-H silylation for the syntheses of planar-chiral metallocene siloles.

Authors:  Qing-Wei Zhang; Kun An; Li-Chuan Liu; Yuan Yue; Wei He
Journal:  Angew Chem Int Ed Engl       Date:  2015-04-23       Impact factor: 15.336

3.  Organosilicon molecules with medicinal applications.

Authors:  Annaliese K Franz; Sean O Wilson
Journal:  J Med Chem       Date:  2012-11-06       Impact factor: 7.446

4.  Remarkably selective iridium catalysts for the elaboration of aromatic C-H bonds.

Authors:  Jian-Yang Cho; Man Kin Tse; Daniel Holmes; Robert E Maleczka; Milton R Smith
Journal:  Science       Date:  2001-11-22       Impact factor: 47.728

5.  C-H functionalization at sterically congested positions by the platinum-catalyzed borylation of arenes.

Authors:  Takayuki Furukawa; Mamoru Tobisu; Naoto Chatani
Journal:  J Am Chem Soc       Date:  2015-09-17       Impact factor: 15.419

6.  Formal Ir-Catalyzed Ligand-Enabled Ortho and Meta Borylation of Aromatic Aldehydes via in Situ-Generated Imines.

Authors:  Ranjana Bisht; Buddhadeb Chattopadhyay
Journal:  J Am Chem Soc       Date:  2015-12-28       Impact factor: 15.419

7.  Construction of Chiral Tetraorganosilicons by Tandem Desymmetrization of Silacyclobutanes/Intermolecular Dehydrogenative Silylation.

Authors:  Qing-Wei Zhang; Kun An; Li-Chuan Liu; Qi Zhang; Huifang Guo; Wei He
Journal:  Angew Chem Int Ed Engl       Date:  2016-12-19       Impact factor: 15.336

8.  Iridium-catalyzed, silyl-directed borylation of nitrogen-containing heterocycles.

Authors:  Daniel W Robbins; Timothy A Boebel; John F Hartwig
Journal:  J Am Chem Soc       Date:  2010-03-31       Impact factor: 15.419

9.  Directed ortho borylation of functionalized arenes catalyzed by a silica-supported compact phosphine-iridium system.

Authors:  Soichiro Kawamorita; Hirohisa Ohmiya; Kenji Hara; Atsushi Fukuoka; Masaya Sawamura
Journal:  J Am Chem Soc       Date:  2009-04-15       Impact factor: 15.419

10.  Rhodium-Catalyzed Enantioselective Silylation of Cyclopropyl C-H Bonds.

Authors:  Taegyo Lee; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2016-06-02       Impact factor: 15.336

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  8 in total

Review 1.  Enantioselective C(sp3)‒H bond activation by chiral transition metal catalysts.

Authors:  Tyler G Saint-Denis; Ru-Yi Zhu; Gang Chen; Qing-Feng Wu; Jin-Quan Yu
Journal:  Science       Date:  2018-02-16       Impact factor: 47.728

2.  Iridium-Catalyzed Silylation of Unactivated C-H Bonds.

Authors:  John F Hartwig; Erik A Romero
Journal:  Tetrahedron       Date:  2019-05-27       Impact factor: 2.457

Review 3.  Asymmetric Catalysis Mediated by Synthetic Peptides, Version 2.0: Expansion of Scope and Mechanisms.

Authors:  Anthony J Metrano; Alex J Chinn; Christopher R Shugrue; Elizabeth A Stone; Byoungmoo Kim; Scott J Miller
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4.  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

5.  Desymmetrization of Diarylmethylamido Bis(phenols) through Peptide-Catalyzed Bromination: Enantiodivergence as a Consequence of a 2 amu Alteration at an Achiral Residue within the Catalyst.

Authors:  Anna E Hurtley; Elizabeth A Stone; Anthony J Metrano; Scott J Miller
Journal:  J Org Chem       Date:  2017-11-03       Impact factor: 4.354

Review 6.  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

Review 7.  Development of Chiral Ligands for the Transition-Metal-Catalyzed Enantioselective Silylation and Borylation of C-H Bonds.

Authors:  Bo Su; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2021-12-21       Impact factor: 16.823

8.  Hydrogen Bond Directed ortho-Selective C-H Borylation of Secondary Aromatic Amides.

Authors:  Shao-Tao Bai; Charles B Bheeter; Joost N H Reek
Journal:  Angew Chem Int Ed Engl       Date:  2019-07-17       Impact factor: 15.336

  8 in total

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