Literature DB >> 24222178

A traceless directing group for C-H borylation.

Sean M Preshlock1, Donald L Plattner, Peter E Maligres, Shane W Krska, Robert E Maleczka, Milton R Smith.   

Abstract

Not a trace: Borylation of the nitrogen in nitrogen heterocycles or anilines provides a traceless directing group for subsequent catalytic C-H borylation. Selectivities that previously required Boc protection can be achieved; furthermore, the NBpin directing group can be installed and removed in-situ, and product yields are substantially higher. Boc=tert-butoxycarbonyl, pin=pinacolato.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  CH activation; anilines; borylation; catalysis; nitrogen heterocycles

Mesh：

Substances：

Year:  2013        PMID： 24222178      PMCID： PMC5032627          DOI： 10.1002/anie.201306511

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


  19 in total

1.  High-throughput optimization of Ir-catalyzed C-H borylation: a tutorial for practical applications.

Authors:  Sean M Preshlock; Behnaz Ghaffari; Peter E Maligres; Shane W Krska; Robert E Maleczka; Milton R Smith
Journal:  J Am Chem Soc       Date:  2013-05-09       Impact factor: 15.419

2.  Ester-directed regioselective borylation of heteroarenes catalyzed by a silica-supported iridium complex.

Authors:  Soichiro Kawamorita; Hirohisa Ohmiya; Masaya Sawamura
Journal:  J Org Chem       Date:  2010-06-04       Impact factor: 4.354

3.  Ortho-C-H borylation of benzoate esters with bis(pinacolato)diboron catalyzed by iridium-phosphine complexes.

Authors:  Tatsuo Ishiyama; Hironori Isou; Takao Kikuchi; Norio Miyaura
Journal:  Chem Commun (Camb)       Date:  2009-11-17       Impact factor: 6.222

4.  Catalytic generation of borenium ions by cooperative B-H bond activation: the elusive direct electrophilic borylation of nitrogen heterocycles with pinacolborane.

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Journal:  J Am Chem Soc       Date:  2013-07-17       Impact factor: 15.419

5.  Electronic effects in iridium C-H borylations: insights from unencumbered substrates and variation of boryl ligand substituents.

Authors:  Britt A Vanchura; Sean M Preshlock; Philipp C Roosen; Venkata A Kallepalli; Richard J Staples; Robert E Maleczka; Daniel A Singleton; Milton R Smith
Journal:  Chem Commun (Camb)       Date:  2010-09-20       Impact factor: 6.222

6.  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

7.  Taking the F out of FLP: simple Lewis acid-base pairs for mild reductions with neutral boranes via borenium ion catalysis.

Authors:  Patrick Eisenberger; Adrian M Bailey; Cathleen M Crudden
Journal:  J Am Chem Soc       Date:  2012-10-10       Impact factor: 15.419

8.  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

9.  Mechanistic studies into amine-mediated electrophilic arene borylation and its application in MIDA boronate synthesis.

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10.  Boc groups as protectors and directors for Ir-catalyzed C-H borylation of heterocycles.

Authors:  Venkata A Kallepalli; Feng Shi; Sulagna Paul; Edith N Onyeozili; Robert E Maleczka; Milton R Smith
Journal:  J Org Chem       Date:  2009-12-04       Impact factor: 4.354
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  22 in total

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

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Journal:  J Am Chem Soc       Date:  2017-05-31       Impact factor: 15.419

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

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4.  Recent Advances in the C-H-Functionalization of the Distal Positions in Pyridines and Quinolines.

Authors:  David E Stephens; Oleg V Larionov
Journal:  Tetrahedron       Date:  2015-08-19       Impact factor: 2.457

5.  Evolution of C-H Bond Functionalization from Methane to Methodology.

Authors:  John F Hartwig
Journal:  J Am Chem Soc       Date:  2015-12-15       Impact factor: 15.419

6.  Sequential Ir/Cu-Mediated Method for the Meta-Selective C-H Radiofluorination of (Hetero)Arenes.

Authors:  Jay S Wright; Liam S Sharninghausen; Sean Preshlock; Allen F Brooks; Melanie S Sanford; Peter J H Scott
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8.  Pyridine-promoted dediazoniation of aryldiazonium tetrafluoroborates: Application to the synthesis of SF5-substituted phenylboronic esters and iodobenzenes.

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9.  Aminoboration: Addition of B-N σ Bonds across C-C π Bonds.

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Journal:  J Am Chem Soc       Date:  2015-08-10       Impact factor: 15.419

Review 10.  Undirected, Homogeneous C-H Bond Functionalization: Challenges and Opportunities.

Authors:  John F Hartwig; Matthew A Larsen
Journal:  ACS Cent Sci       Date:  2016-05-02       Impact factor: 14.553
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