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Catalyzed organic reactions that produce an organoboron compound
Metal-catalyzed C–H borylation reactions are transition metal catalyzed organic reactions that produce an organoboron compound through functionalization
Borylation
Chemical reaction
Miyaura borylation, also known as the Miyaura borylation reaction, is a named reaction in organic chemistry that allows for the generation of boronates
Miyaura_borylation
Chemical catalyst
and competes with hydrogen activation. Amine-borane FLPs catalyse the borylation of electron-rich aromatic heterocycles (Scheme 1). The reaction is driven
Frustrated_Lewis_pair
Chemical compound
B2(OH)4 + 2 NaCl + 4 HCl Tetrahydrodiboron can be used in the Miyaura borylation of aryl halides and pseudo-halides to form aryl boronic acids, which are
Tetrahydroxydiboron
Group of organonitrogen compounds
of benzoyl peroxide (2 mol %) as an initiator: Alternatively similar borylation can be achieved using transition metal carbonyl complexes including dimanganese
Diazonium_compound
Japanese Chemist
cyclic and acyclic enones. The Miyaura-Ishiyama borylation reaction is also known as the Miyaura borylation reaction. In this reaction, a catalytic system
Norio_Miyaura
Organic reaction
and release the product. Transforming C-H bonds into C-B bonds through borylation has been thoroughly investigated due to their utility in synthesis (i
Carbon–hydrogen bond activation
Carbon–hydrogen_bond_activation
have also been implicated as intermediates in electrophilic aromatic borylation reactions. In many examples of this reaction, a catalyst is used to activate
Boranylium_ions
Study of compounds containing a boron-carbon bond
reagents. One common cyclic organoboron reagent is 9-BBN. Metal-catalyzed borylation reactions produce an organoboron compound from aliphatic or aromatic C-H
Organoboron_chemistry
Chemical compound
of aldehydes, ketones, and carboxylic acids. Pinacolborane is used in borylation, a form of C-H activation. Dehydrogenation of pinacolborane affords dipinacolatodiborane
Pinacolborane
Organic compound of the form R–B(OH)2
triflates with diboronyl esters in a coupling reaction known as the Miyaura borylation reaction. An alternative to esters in this method is the use of diboronic
Boronic_acid
Cross-coupling reaction between boronic acid & an organohalide
synthesis. This reaction is sometimes telescoped with the related Miyaura borylation; the combination is the Suzuki–Miyaura reaction. It is widely used to
Suzuki_reaction
American organometallic chemist (born 1964)
trifluoromethanesulfonate): Also while at Yale, he discovered the metal-catalyzed borylation of unactivated C-H bonds. In 2006, he assumed the Kenneth L. Reinhart
John_F._Hartwig
Field of study
- are required to stabilize Rh(V). This oxidation state is invoked in borylation reactions. Cyclometalated rhodium compounds constitute an important class
Organorhodium_chemistry
Chemical element with atomic number 77 (Ir)
doi:10.1021/ja00377a032. Hartwig, John F. (2011). "Regioselectivity of the Borylation of Alkanes and Arenes". Chemical Society Reviews. 40 (4): 1992–2002. doi:10
Iridium
Type of saturated hydrocarbon compound
; Hartwig, John F. (2023). "Transition-Metal-Catalyzed Silylation and Borylation of C–H Bonds for the Synthesis and Functionalization of Complex Molecules"
Alkane
Chemical compound
Stereocontrolled Synthesis of the 2-ene-1,4-diol Core through a Lithiation–Borylation–Allylation Sequence". Angewandte Chemie International Edition. 49 (37):
Tetrahydropyran
American organometallic chemistry professor
Irvine. Blum works on mechanistic chemistry, most recently focusing on borylation reactions and the development of single-molecule and single-particle fluorescence
Suzanne_Blum
Chemical compound
Frédéric-Georges (2019-08-07). "Isodesmic C–H Borylation: Perspectives and Proof of Concept of Transfer Borylation Catalysis". Journal of the American Chemical
2-Mercaptopyridine
Chemical compound
synthesis of hindered tertiary boronic esters under in situ lithiation–borylation conditions". Chemical Communications. 52 (30): 5289–5292. doi:10.1039/C6CC00536E
Neopentyl_glycol
Chemical compound
conversion of an aryl halide to a phenol (the first step is a Miyaura borylation). In the European Union, sodium perborate, like most other inorganic boron
Sodium_perborate
Chemical reaction
Heck-type termination with olefins, Suzuki-type reaction with boronic esters, borylation with bis(pinacolato)diboron, protonation with i-PrOH, decarboxylative
Catellani_reaction
of symmetrical and unsymmetrical cyclic diborenes via NHC-directed C–H borylation". Chemical Science. 16 (25): 11637–11643. doi:10.1039/D5SC03150H. PMC 12127849
2,6-Diisopropylphenyl_group
Phosphorus-containing ligands
wide array of reactions, including the arylation of ketones and esters, borylation of aryl chlorides, and the arylation of indoles. Many modified versions
Dialkylbiaryl phosphine ligands
Dialkylbiaryl_phosphine_ligands
Chemical compound
9b13602. PMID 32216315. Schmid, L.; Chábera, P.; Rüter, I.; et al. (2022). "Borylation in the second coordination sphere of FeII cyanido complexes and its impact
Tris(bipyridine)iron(II) chloride
Tris(bipyridine)iron(II)_chloride
Chemical reaction
installation of adjacent tertiary benzylic stereocentres using lithiation–borylation–protodeboronation methodology. Application to the synthesis of bifluranol
Protodeboronation
Chemical compound
ring, and both have been synthesised involving ligand-controlled C–H borylation. Borthwick AD (2012). "2,5-Diketopiperazines: Synthesis, Reactions, Medicinal
Verruculogen
9-step process starting with 1,3-dibromobenzene, which involves several borylation and coupling steps. A variant that is doped with nitrogen has also been
Phenine_nanotube
American chemist
Matzger, A. J.; Sanford, M. S. "Catalyst-Controlled Selectivity in the C–H Borylation of Methane and Ethane," Science 2016, 351, 1421–1424. Camasso, N. M.;
Melanie_Sanford
American organic chemist (born 1977)
Decarboxylative Borylation (2017) Decarboxylative Alkenylation (2017) Decarboxylative Alkynylation (2017) Cu-Catalyzed Decarboxylative Borylation (2018) Ni-Electrocatalytic
Phil_S._Baran
heterobimetallic bond-breaking process is also employed in the IPrCuFp-catalyzed C-H borylation system developed by Mankad (Scheme 5). Bimetallic cleavage of the B-H
Heterobimetallic_catalysis
Group of chemical elements
*; Marks, T.J.* Chemodivergent Organolanthanide Catalyzed C-H a-Mono-Borylation of Pyridines. J. Am. Chem. Soc. 2022, 144, 17086-17096: https://pubs.acs
Group_3_element
British chemist
M. Mansell; L. Maron; D. McKay (2012). "Spontaneous reduction and C–H borylation of arenes mediated by uranium(III) disproportionation". Nature Chemistry
Polly_Arnold
Class of chemical substances
list (link) Li Zhang, Lei Jiao (2017-01-18), "Pyridine-Catalyzed Radical Borylation of Aryl Halides", Journal of the American Chemical Society, vol. 139,
Pyridines
Drugs that inhibit β-Lactamase enzymes
to Ser70 and stabilizes the molecule by being hydrophobic. This makes borylation occur frequently and deborylation occur very rarely. Comparing it to its
Β-Lactamase_inhibitor
related pinacolborane, are intermediates in transition metal-catalyzed borylation reactions. Oxidative addition is the main route to metal boryl complexes
Transition metal boryl complex
Transition_metal_boryl_complex
Family of chemical compounds
biologically-relevant asymmetric catalysis such as asymmetric conjugate borylation (ACB). Inclusion of a chiral center on the CAAC ligand allows for the
Cyclic_alkyl_amino_carbenes
Chemical compound
Suzuki-Miyaura couplings, Sonogashira couplings, Huisgen cycloadditions, and borylations. Under the catalysis of platinum, it reacts with hydrogen to produce
1-Decyne
addition reaction with 1,4-benzoquinone yielded a syn-cyclohexadiene moiety. Borylation of this material followed macrocyclization under Suzuki–Miyuara cross-coupling
Cycloparaphenylene
Chemical compound
2017). "Tris(pentafluorophenyl)borane and Beyond: Modern Advances in Borylation Chemistry". Inorganic Chemistry. 56 (15): 8627–8643. doi:10.1021/acs.inorgchem
Tris(pentafluorophenyl)borane
Chemical process
Michael J.; Thomas, Stephen P. (2021-09-13). "Aluminium-Catalyzed C(sp)−H Borylation of Alkynes". Angewandte Chemie. 133 (38): 20840–20845. Bibcode:2021AngCh
Semi-hydrogenation_of_alkynes
Class of boron heterocyclic compounds
mechanisms The most widely used synthetic route to DBA utilizes electrophilic borylation chemistry as the key transformation, which dates to 1969 from Seibert
Diboraanthracene
Minisci reaction Mislow–Evans rearrangement Mitsunobu reaction Miyaura borylation Modified Wittig-Claisen tandem reaction Molisch's test Mozingo reduction
List_of_organic_reactions
Chemical compound
Alfredo (2013-02-06). "Electronic and Structural Effects of Stepwise Borylation and Quaternization on Borirene Aromaticity". Journal of the American Chemical
Borirene
Complexes: Synthesis, Structures and Applications in the Catalytic C−H Borylation of Arenes and Alkanes". Chemistry – A European Journal. 27 (71): 17824–17833
Transition metal alkenyl complex
Transition_metal_alkenyl_complex
Process of converting methane to another molecule
electrophilic activation (Shilov system, see above), dehydrogenation, borylation, hydrogen-deuterium exchange, and carbene/nitrene/oxo insertion. The functionalization
Methane_functionalization
doi:10.1021/ja00377a032. Hartwig, John F. (2011). "Regioselectivity of the Borylation of Alkanes and Arenes". Chemical Society Reviews. 40 (4): 1992–2002. doi:10
Iridium_compounds
Chemistry of compounds with W-C bonds
Computational Evidence for a Boron-Assisted, σ-Bond Metathesis Pathway for Alkane Borylation". Journal of the American Chemical Society. 125 (4): 858–859. Bibcode:2003JAChS
Organotungsten_chemistry
Chiral ligands
ligand allowed for C(sp3)–H functionalization via arylation of α-methyls, borylation of cyclobutyl carboxylic amides, and boronic cross coupling of alkyl amines
Mono-N-protected_amino_acids
González-Moreiras, S. Ahn, M. R. Smith 3rd, M.-H. Baik, D. J. Mindiola, Catalytic borylation of methane, Science 351, 1424–1427 (2016). https://www.science.org/doi/10
Daniel_Mindiola
Overview of and topical guide to organic chemistry
Larock indole synthesis Liebeskind-Srogl coupling McMurry reaction Miyaura borylation Negishi coupling Phosphonium coupling Pinacol coupling Prins reaction
Outline_of_organic_chemistry
Boron containing acene compounds
Boron-Doped Polycyclic Aromatic Hydrocarbons by General One-Pot C–H Borylations". Journal of the American Chemical Society. 141 (22): 9096–9104. doi:10
Boraacenes
Lin, L. Q. H.; Loh, K. P.; Koh, M. J. (2020). "Site-selective alkene borylation enabled by synergistic hydrometallation and borometallation". Nature Catalysis
Ming_Joo_Koh
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