Literature DB >> 23534698

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

Sean M Preshlock1, Behnaz Ghaffari, Peter E Maligres, Shane W Krska, Robert E Maleczka, Milton R Smith.   

Abstract

With the aid of high-throughput screening, the efficiency of Ir-catalyzed C-H borylations has been assessed as functions of precatalyst, boron reagent, ligand, order of addition, temperature, solvent, and substrate. This study not only validated some accepted practices but also uncovered unconventional conditions that were key to substrate performance. We anticipate that insights drawn from these findings will be used to design reaction conditions for substrates whose borylations are difficult to impossible using standard catalytic conditions.

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Year:  2013        PMID: 23534698     DOI: 10.1021/ja400295v

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


  29 in total

1.  Next-Generation Total Synthesis of Vancomycin.

Authors:  Maxwell J Moore; Shiwei Qu; Ceheng Tan; Yu Cai; Yuzo Mogi; D Jamin Keith; Dale L Boger
Journal:  J Am Chem Soc       Date:  2020-09-04       Impact factor: 15.419

2.  C(sp2)-H Borylation of Fluorinated Arenes Using an Air-Stable Cobalt Precatalyst: Electronically Enhanced Site Selectivity Enables Synthetic Opportunities.

Authors:  Jennifer V Obligacion; Máté J Bezdek; Paul J Chirik
Journal:  J Am Chem Soc       Date:  2017-02-10       Impact factor: 15.419

3.  Total Synthesis of Verruculogen and Fumitremorgin A Enabled by Ligand-Controlled C-H Borylation.

Authors:  Yu Feng; Dane Holte; Jochen Zoller; Shigenobu Umemiya; Leah R Simke; Phil S Baran
Journal:  J Am Chem Soc       Date:  2015-08-11       Impact factor: 15.419

4.  Nickel-catalyzed borylation of halides and pseudohalides with tetrahydroxydiboron [B2(OH)4].

Authors:  Gary A Molander; Livia N Cavalcanti; Carolina García-García
Journal:  J Org Chem       Date:  2013-06-18       Impact factor: 4.354

5.  Bismuth Acetate as a Catalyst for the Sequential Protodeboronation of Di- and Triborylated Indoles.

Authors:  Fangyi Shen; Sriram Tyagarajan; Damith Perera; Shane W Krska; Peter E Maligres; Milton R Smith; Robert E Maleczka
Journal:  Org Lett       Date:  2016-03-21       Impact factor: 6.005

6.  Effect of Ligand Structure on the Electron Density and Activity of Iridium Catalysts for the Borylation of Alkanes.

Authors:  Matthew A Larsen; Raphael J Oeschger; John F Hartwig
Journal:  ACS Catal       Date:  2020-02-11       Impact factor: 13.084

7.  A traceless directing group for C-H borylation.

Authors:  Sean M Preshlock; Donald L Plattner; Peter E Maligres; Shane W Krska; Robert E Maleczka; Milton R Smith
Journal:  Angew Chem Int Ed Engl       Date:  2013-11-12       Impact factor: 15.336

8.  Direct C7 Functionalization of Tryptophan. Synthesis of Methyl (S)-2-((tert-Butoxycarbonyl)amino)-3-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-3-yl)propanoate.

Authors:  Kazuma Amaike; Richard P Loach; Mohammad Movassaghi
Journal:  Organic Synth       Date:  2015

9.  Origin of the Difference in Reactivity between Ir Catalysts for the Borylation of C-H Bonds.

Authors:  Raphael J Oeschger; Matthew A Larsen; Alessandro Bismuto; John F Hartwig
Journal:  J Am Chem Soc       Date:  2019-10-03       Impact factor: 15.419

Review 10.  Digitising chemical synthesis in automated and robotic flow.

Authors:  Tomas Hardwick; Nisar Ahmed
Journal:  Chem Sci       Date:  2020-10-07       Impact factor: 9.825

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