Enabling Catalytic Cross Couplings with only Zinc Electrophiles, Nucleophiles and Boranes

Project Information

ECO-ZEN

Grant agreement ID: 769599

DOI

10.3030/769599

Project closed

EC signature date 22 January 2018

Start date 1 May 2018

End date 30 April 2024

Funded under

• EXCELLENT SCIENCE - European Research Council (ERC)

Total cost

€ 2 070 093,00

EU contribution

€ 2 070 093,00

Coordinated by

THE UNIVERSITY OF EDINBURGH
United Kingdom

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Links to deliverables and publications from FP7 projects, as well as links to some specific result types such as dataset and software, are dynamically retrieved from OpenAIRE .

Publications

Peer reviewed articles (27)

Developing organoboranes as phase transfer catalysts fornucleophilic fluorination using CsF

Author(s): Kirschner, S, Peters, M, Uzelac, M, Yuan, K & Ingleson, MJ
Published in: Chemical Science, Issue 13, 2022, Page(s) 2661–2668, ISSN 2041-6539
Publisher: Royal Society of Chemistry
DOI: 10.1039/d2sc00303a

Borylation–Reduction–Borylation for the Formation of 1,4-Azaborines

Author(s): Shantaram S. Kothavale, Saqib A. Iqbal, Emily L. Hanover, Abhishek K. Gupta, Eli Zysman-Colman, Michael J. Ingleson
Published in: Organic Letters, Issue 25, 2023, Page(s) 8912-8916, ISSN 1523-7060
Publisher: American Chemical Society
DOI: 10.1021/acs.orglett.3c03731

Zinc catalysed electrophilic C–H borylation of heteroarenes

Author(s): M. E. Grundy, K. Yuan, G. Nichol, M. J. Ingleson
Published in: Chemical Science, Issue Volume 12, 2021, Page(s) 8190-8198, ISSN 2041-6539
Publisher: Royal Society of Chemistry
DOI: 10.1039/d1sc01883c

Intramolecular (directed) electrophilic C–H borylation

Author(s): S. A. Iqbal, J. Pahl, K. Yuan, M. J. Ingleson
Published in: Chemical Society Reviews, Issue 49/13, 2020, Page(s) 4564-4591, ISSN 0306-0012
Publisher: Royal Society of Chemistry
DOI: 10.1039/c9cs00763f

Formation of a hydride containing amido-zincate usingpinacolborane

Author(s): Uzelac, M, Yuan, K, Nichol, GS & Ingleson, MJ
Published in: Dalton Transactions, Issue 50, 2021, Page(s) 14018-14026, ISSN 1477-9234
Publisher: Royal Society of Chemistry
DOI: 10.1039/d1dt02580e

Amides as modifiable directing groups in electrophilic borylation

Author(s): Saqib A. Iqbal; Marina Uzelac; Ismat Nawaz; Zhongxing Wang; T. Harri Jones; Kang Yuan; Clement R. P. Millet; Gary S. Nichol; Ghayoor Abbas Chotana; Michael J. Ingleson
Published in: Chemical Science, 2023, Page(s) 3865-3872, ISSN 2041-6539
Publisher: Royal Society of Chemistry
DOI: 10.1039/d2sc06483a

Borylation Directed Borylation of Indoles Using Pyrazabole Electrophiles: A One‐Pot Route to C7‐Borylated‐Indolines

Author(s): Jürgen Pahl; Emily Noone; Marina Uzelac; Kang Yuan; Michael J. Ingleson
Published in: Angewandte Chemie International Edition, 2022, Page(s) e202206230, ISSN 1521-3773
Publisher: WILEY
DOI: 10.1002/anie.202206230

Synthesis of Electrophiles Derived from Dimeric Aminoboranes and Assessing Their Utility in the Borylation of π Nucleophiles

Author(s): Clément R. P. Millet; Jürgen Pahl; Emily Noone; Kang Yuan; Gary S. Nichol; Marina Uzelac; Michael J. Ingleson
Published in: Organometallics, 2022, Page(s) 2638–2647, ISSN 1520-6041
Publisher: American Chemical Society
DOI: 10.1021/acs.organomet.2c00393

Haloboration: scope, mechanism and utility

Author(s): Sven Kirschner, Kang Yuan, Michael J. Ingleson
Published in: New Journal of Chemistry, 2020, ISSN 1144-0546
Publisher: Royal Society of Chemistry
DOI: 10.1039/d0nj02908d

NacNac-zinc-pyridonate mediated ε-caprolactone ROP

Author(s): Jack W. J. Hughes, Dawid J. Babula, Findlay Stowers-Veitch, Kang Yuan, Marina Uzelac, Gary S. Nichol, Michael J. Ingleson, Jennifer A. Garden
Published in: Dalton Transactions, Issue 52, 2024, Page(s) 17767-17775, ISSN 1477-9226
Publisher: Royal Society of Chemistry
DOI: 10.1039/d3dt03344a

A Comparison of Two Zinc Hydride Catalysts for Terminal Alkyne C–H Borylation/Hydroboration and the Formation of 1,1,1-Triborylalkanes by Tandem Catalysis Using Zn–H and B–H Compounds

Author(s): Marina Uzelac, Kang Yuan, Michael J. Ingleson
Published in: Organometallics, Issue 39/8, 2020, Page(s) 1332-1338, ISSN 0276-7333
Publisher: American Chemical Society
DOI: 10.1021/acs.organomet.0c00086

Enhanced N-directed electrophilic C-H borylation generates BN-[5]- and [6]helicenes with improved photophysical properties.

Author(s): Yuan, K, Volland, D, Kirschner, S, Uzelac, M, Nichol, GS, Nowak-krol, A & Ingleson, MJ
Published in: Chemical Science, Issue 13, 2022, Page(s) 1136–1145, ISSN 2041-6539
Publisher: Royal Society of Chemistry
DOI: 10.1039/d1sc06513k

Low-Coordinate NHC–Zinc Hydride Complexes Catalyze Alkyne C–H Borylation and Hydroboration Using Pinacolborane

Author(s): Richard J. Procter, Marina Uzelac, Jessica Cid, Philip J. Rushworth, Michael J. Ingleson
Published in: ACS Catalysis, Issue 9/6, 2019, Page(s) 5760-5771, ISSN 2155-5435
Publisher: American Chemical Society
DOI: 10.1021/acscatal.9b01370

The synthesis of brominated-boron-doped PAHs by alkyne 1,1-bromoboration: mechanistic and functionalisation studies

Author(s): K. Yuan, R. J. Kahan, C. Si, A. Williams, S. Kirschner, M. Uzelac, E. Zysman-Colman, M. J. Ingleson
Published in: Chemical Science, Issue 11/12, 2020, Page(s) 3258-3267, ISSN 2041-6520
Publisher: Royal Society of Chemistry
DOI: 10.1039/c9sc05404a

Borylative cyclisation of diynes using BCl 3 and borocations

Author(s): Andrew J. Warner, Kieron M. Enright, John M. Cole, Kang Yuan, John S. McGough, Michael J. Ingleson
Published in: Organic & Biomolecular Chemistry, Issue 17/22, 2019, Page(s) 5520-5525, ISSN 1477-0520
Publisher: Royal Society of Chemistry
DOI: 10.1039/c9ob00991d

Transition Metal‐Free Catalytic C−H Zincation and Alumination

Author(s): Milan Kumar Bisai, Justyna Łosiewicz, Lia Sotorrios, Gary S. Nichol, Andrew P. Dominey, Michael J. Cowley, Stephen P. Thomas, Stuart A. Macgregor, Michael J. Ingleson
Published in: Angewandte Chemie International Edition, Issue 63, 2024, ISSN 1433-7851
Publisher: John Wiley & Sons Ltd.
DOI: 10.1002/anie.202404848

Two Directing Groups Used for Metal Catalysed Meta-C−H Functionalisation Only Effect Ortho Electrophilic C−H Borylation

Author(s): Saqib A. Iqbal, Clement R. P. Millet, Jürgen Pahl, Kang Yuan, Michael J. Ingleson
Published in: European Journal of Organic Chemistry, 2022, Page(s) e202200901, ISSN 1099-0690
Publisher: WILEY-VCH
DOI: 10.1002/ejoc.202200901

Controlling selectivity in N-heterocycle directed borylation ofindoles

Author(s): Iqbal, SA, Yuan, K, Cid, J, Pahl, J & Ingleson, MJ
Published in: Organic & Biomolecular chemistry, Issue Volume 19, 2021, Page(s) 2949-2958, ISSN 1477-0539
Publisher: Royal Society of Chemistry
DOI: 10.1039/d1ob00018g

Main Group Catalyzed Arene Borylation: Challenges and Opportunities

Author(s): Michael J. Ingleson
Published in: ACS Catalysis, 2023, Page(s) 7691–7697, ISSN 2155-5435
Publisher: American Chemical Society
DOI: 10.1021/acscatal.3c01668

Reductive α-borylation of α,β-unsaturated esters using NHC–BH 3 activated by I 2 as a metal-free route to α-boryl esters

Author(s): James E. Radcliffe, Valerio Fasano, Ralph W. Adams, Peiran You, Michael J. Ingleson
Published in: Chemical Science, Issue 10/5, 2019, Page(s) 1434-1441, ISSN 2041-6520
Publisher: Royal Society of Chemistry
DOI: 10.1039/c8sc04305a

Synthesis, Characterization, and Functionalization of 1-Boraphenalenes

Author(s): Rachel J. Kahan, Daniel L. Crossley, Jessica Cid, James E. Radcliffe, Michael J. Ingleson
Published in: Angewandte Chemie International Edition, Issue 57/27, 2018, Page(s) 8084-8088, ISSN 1433-7851
Publisher: John Wiley & Sons Ltd.
DOI: 10.1002/anie.201803180

Selective Boryl-Anion Migration in a Vinyl sp 2 −sp 3 Diborane Induced by Soft Borane Lewis Acids

Author(s): Valerio Fasano, Jessica Cid, Richard J. Procter, Emily Ross, Michael J. Ingleson
Published in: Angewandte Chemie International Edition, Issue 57/40, 2018, Page(s) 13293-13297, ISSN 1433-7851
Publisher: John Wiley & Sons Ltd.
DOI: 10.1002/anie.201808216

Understanding and Expanding Zinc Cation/Amine Frustrated Lewis Pair Catalyzed C–H Borylation

Author(s): Matthew E. Grundy; Lia Sotorrios; Milan Kumar Bisai; Kang Yuan; Stuart A. Macgregor; Michael J. Ingleson
Published in: ACS Catalysis, 2022, Page(s) 2286–2294, ISSN 2155-5435
Publisher: American Chemical Society
DOI: 10.1021/acscatal.2c05995

Borylation directed borylation of <i>N</i>-alkyl anilines using iodine activated pyrazaboles

Author(s): C. R. P. Millet, E. Noone, A. V. Schellbach, J. Pahl, J. Łosiewicz, G. S. Nichol, M. J. Ingleson
Published in: Chemical Science, Issue 14, 2024, Page(s) 12041-12048, ISSN 2041-6520
Publisher: Royal Society of Chemistry
DOI: 10.1039/d3sc04269c

Acyl‐Directed ortho ‐Borylation of Anilines and C7 Borylation of Indoles using just BBr 3

Author(s): Saqib A. Iqbal, Jessica Cid, Richard J. Procter, Marina Uzelac, Kang Yuan, Michael J. Ingleson
Published in: Angewandte Chemie International Edition, Issue 58/43, 2019, Page(s) 15381-15385, ISSN 1433-7851
Publisher: John Wiley & Sons Ltd.
DOI: 10.1002/anie.201909786

Brominated B₁-Polycyclic Aromatic Hydrocarbons for the Synthesis of Deep-Red to Near-Infrared Delayed Fluorescence Emitters

Author(s): Kang Yuan; Abhishek Kumar Gupta; Changfeng Si; Marina Uzelac; Eli Zysman-Colman; Michael James Ingleson
Published in: Organic Letters, 2023, Page(s) 5880–5884, ISSN 1523-7052
Publisher: American Chemical Society
DOI: 10.1021/acs.orglett.3c02167

Haloboration of o-Alkynyl Phenols Generates Halogenated Bicyclic-Boronates

Author(s): Kang Yuan, Michael James Ingleson
Published in: Angewandte Chemie International Edition, 2023, Page(s) e202301463, ISSN 1521-3773
Publisher: WILEY-VCH
DOI: 10.1002/anie.202301463