Main Group Catalyzed Arene Borylation: Challenges and Opportunities

Autor: Michael J. Ingleson

Publikováno v: Ingleson, M J 2023, ' Main Group Catalyzed Arene Borylation: Challenges and Opportunities ', ACS Catalysis, pp. 7691-7697 . https://doi.org/10.1021/acscatal.3c01668

C–H borylation is an efficient method to generate organoboranes that are powerful intermediates in synthesis, due in large part to the Suzuki–Miyaura reaction. (1) Tremendous advances have been made using transition metal based catalysts for aren

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::ae456abacc003f60c10d02e8fc7dacd8
https://doi.org/10.1021/acscatal.3c01668

Amides as modifiable directing groups in electrophilic borylation

Autor: 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

Publikováno v: Iqbal, S A, Uzelac, M, Nawaz, I, Wang, Z, Jones, T H, Yuan, K, Millet, C R P, Nichol, G S, Chotana, G A & Ingleson, M J 2023, ' Amides as modifiable directing groups in electrophilic borylation ', Chemical Science . https://doi.org/10.1039/D2SC06483A

Amide directed C–H borylation using ≥two equiv. of BBr3 forms borenium cations containing a R2N(R′)C[double bond]O→B(Ar)Br unit which has significant Lewis acidity at the carbonyl carbon. This enables reduction of the amide unit to an amine u

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::7a885899713facec175edf967e81e5e3
https://doi.org/10.1039/d2sc06483a

Developing organoboranes as phase transfer catalysts for nucleophilic fluorination using CsF

Autor: Sven Kirschner, Matthew Peters, Kang Yuan, Marina Uzelac, Michael J. Ingleson

Publikováno v: Chemical Science
Kirschner, S, Peters, M, Uzelac, M, Yuan, K & Ingleson, M J 2022, ' Developing organoboranes as phase transfer catalysts for nucleophilic fluorination using CsF ', Chemical Science . https://doi.org/10.1039/D2SC00303A

Despite the general high fluorophilicity of boron, organoboranes such as BEt3 and 3,5-(CF3)2C6H3–BPin are shown herein for the first time, to our knowledge, to be effective (solid to solution) phase-transfer catalysts for the fluorination of certai

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https://doi.org/10.1039/d2sc00303a

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

Autor: Saqib A. Iqbal, Clement R. P. Millet, Jürgen Pahl, Kang Yuan, Michael J. Ingleson

Publikováno v: Iqbal, S A, Millet, C R P, Pahl, J, Yuan, K & Ingleson, M 2022, ' Two Directing Groups Used for Metal Catalysed Meta-C–H Functionalisation Only Effect Ortho Electrophilic C–H Borylation ', European Journal of Organic Chemistry, vol. 2022, no. 44, e202200901 . https://doi.org/10.1002/ejoc.202200901

Two templates used in meta-directed C–H functionalisation under metal catalysis do not direct meta C–H borylation under electrophilic borylation conditions. Using BCl3 only Lewis adduct formation with Lewis basic sites in the template is observed

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::7b3ca7660172fbce3d2c69ec2068c7a2
https://www.pure.ed.ac.uk/ws/files/315807896/20221221_Ingleson_Eur_J_Org_Chem_VoR.pdf

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

Autor: Jürgen Pahl, Emily Noone, Marina Uzelac, Kang Yuan, Michael J. Ingleson

Publikováno v: Pahl, J, Noone, E, Uzelac, M, Yuan, K & Ingleson, M 2022, ' Borylation Directed Borylation of Indoles Using Pyrazabole Electrophiles: A One-Pot Route to C7-Borylated-Indolines ', Angewandte Chemie International Edition . https://doi.org/10.1002/anie.202206230

Pyrazabole ( 1 ) is a readily accessible diboron compound that can be transformed into ditopic electrophiles. In 1 (and derivatives), the B∙∙∙B separation is ca. 3 Å, appropriate for one boron centre bonding to N and one to the C7 of indoles a

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::61a8ce22f23cfdf97e8b8185a98e7bde
https://doi.org/10.1002/anie.202206230