Literature DB >> 25778434

Nickel-catalyzed borylation of arenes and indoles via C-H bond cleavage.

Takayuki Furukawa1, Mamoru Tobisu, Naoto Chatani.   

Abstract

The first nickel-catalyzed method for the borylation of carbon-hydrogen bonds in arenes and indoles is described. The use of an N-heterocyclic carbene ligand is essential for an efficient reaction, with an N-cyclohexyl-substituted derivative being optimal. This method is readily applied to the gram scale synthesis of 2-borylindole.

Entities:  

Year:  2015        PMID： 25778434     DOI： 10.1039/c5cc01378j

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  16 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.  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.  Palladium Catalyzed Asymmetric Three-Component Coupling of Boronic Esters, Indoles, and Allylic Acetates.

Authors:  Santanu Panda; Joseph M Ready
Journal:  J Am Chem Soc       Date:  2017-04-21       Impact factor: 15.419

Review 5.  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

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

Review 8.  N-Heterocyclic Carbene Complexes in C-H Activation Reactions.

Authors:  Qun Zhao; Guangrong Meng; Steven P Nolan; Michal Szostak
Journal:  Chem Rev       Date:  2020-01-22       Impact factor: 60.622

9.  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

10.  Selective Benzylic CH-Borylations by Tandem Cobalt Catalysis.

Authors:  Pradip Ghosh; Roland Schoch; Matthias Bauer; Axel Jacobi von Wangelin
Journal:  Angew Chem Int Ed Engl       Date:  2021-11-22       Impact factor: 16.823
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