Article
Chemistry, Multidisciplinary
Paula Dominguez-Molano, Gerard Bru, Oriol Salvado, Ricardo J. Maza, Jorge J. Carbo, Elena Fernandez
Summary: The exchange of boryl moieties between alkenylboranes and diboron reagents is proposed as a stereospecific cross-metathesis pathway, leading to the formation of mixed diboron reagents. Density functional theory calculations suggest a mechanism for stereocontrolled C(sp(2))-B/B'-B' cross-metathesis with both symmetric and non-symmetric diboron reagents.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Qi Tang, Shi-Jun Li, Xiaohan Ye, Teng Yuan, Kai Zhao, Ying He, Chuan Shan, Lukasz Wojtas, David Richardson, Yu Lan, Xiaodong Shi
Summary: A new class of stable four-coordinated benzotriazole-borane compounds was developed via gold-catalyzed alkyne hydroboration. These compounds showed excellent stability, strong and tunable fluorescence emission, and easy synthesis, making them interesting new fluorescent probes for future chemical and biological applications.
Article
Chemistry, Multidisciplinary
Fabian Schorr, Nils Schopper, Nicolas Riensch, Felipe Fantuzzi, Marco Neder, Rian D. Dewhurst, Torsten Thiess, Tobias Brueckner, Kai Hammond, Holger Helten, Maik Finze, Holger Braunschweig
Summary: Novel alkynyl-functionalized diarylbis(dimethylamino)diboranes(4) were prepared by salt metathesis, and their appended alkynyl groups underwent hydroboration to yield discrete boryl-appended diborane(4) species when reacted with monohydroboranes. Conversely, reactions with dihydroboranes led to the formation of oligomeric species with B-B bonds, with some exhibiting good air stability and solubility in common organic solvents. These oligomeric species, characterized by NMR, vibrational spectroscopy, and size-exclusion chromatography, can contain up to ten repeat units.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Danijela Lunic, Nil Sanosa, Ignacio Funes-Ardoiz, Christopher J. Teskey
Summary: Although challenges still exist, we have developed a simple and mild protocol that selectively reduces starting materials containing both more nucleophilic and more electrophilic groups at room temperature. This protocol is able to preserve the integrity of other functional groups.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Inorganic & Nuclear
Qingheng Lai, Oleg Ozerov
Summary: The catalytic dehydrogenative diboration (DHDB) of alkyne with HBpin was successfully achieved using Ir precursors under CO atmosphere, with higher selectivity in less polar solvents and higher CO pressure. the addition of a catalytic amount of tBuNC further improved the selectivity, leading to isolation of some DHDB products on the preparative scale.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Jingjing Wang, Haiyu Zhou, Junhui Wei, Fei Liu, Tongdao Wang
Summary: The first alkyne trans-hydroboration reaction without a B-H bond was achieved by reacting propargyl amines with Lewis acidic boranes under mild conditions. The mechanism involved borane-mediated alkyne activation and intramolecular hydride transfer, resulting in a unique hydroboration in the absence of a B-H bond.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Inorganic & Nuclear
Karel Skoch, Constantin G. Daniliuc, Gerald Kehr, Gerhard Erker
Summary: Two different ferrocene derivatives reacted with hydroboration reagents, resulting in boron-containing cyclic compounds and further formation of dimeric bis-boron containing macrocyclic bridged bis-ferrocene systems with different structures.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2022)
Review
Chemistry, Inorganic & Nuclear
Urminder Kaur, Koushik Saha, Sourav Gayen, Sundargopal Ghosh
Summary: Transition metal complexes of boron with tri-coordinated boron have unique bonding patterns and reactivity towards organic substrates, serving as key intermediates in many catalytic cycles. This field has recently garnered significant attention for developing new molecules.
COORDINATION CHEMISTRY REVIEWS
(2021)
Article
Chemistry, Organic
Filip Meger, Alexander C. W. Kwok, Franziska Gilch, Dominic R. Willcox, Alex J. Hendy, Kieran Nicholson, Andrew D. Bage, Thomas Langer, Thomas A. Hunt, Stephen P. Thomas
Summary: In this study, a borane-catalysed hydroboration of nitriles to give primary amines is reported, with good yields and chemoselectivity observed. DFT calculations and mechanistic studies support the proposal of a double B-N/B-H transborylation mechanism.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Lara Tejerina, Jorge Labella, Lara Martinez-Fernandez, Ines Corral, M. Victoria Martinez-Diaz, Tomas Torres
Summary: The research successfully prepared SubPc hydride derivatives for the first time by utilizing the electrophilic character of DIBAL-H, allowing for axial functionalization of SubPcs and providing a new synthetic method for the development of organic photovoltaic devices.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Yuichiro Mutoh, Kensuke Yamamoto, Yusei Mohara, Shinichi Saito
Summary: Efforts were made to develop a ruthenium complex for efficient catalysis of the hydrosilylation and hydroboration of terminal alkynes, as well as to explore factors controlling the (Z)-selectivity of the reactions. Additionally, the activation of B-protected boronic acids, R-B(dan) (dan = naphthalene-1,8-diaminato), believed to not participate in Suzuki-Miyaura cross-coupling, was discussed.
Article
Chemistry, Multidisciplinary
Pinaki Nad, Arup Mukherjee
Summary: A metal-free and sustainable method has been developed for the reduction of unprotected indoles. The catalytic system, consisting of B(C6F5)3 and THF as a Lewis acid-base pair, can activate the B-H bond of pincolborane. The catalytic system shows a broad substrate scope. Control experiments were conducted to understand the possible catalytic intermediates involved.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Physical
Kieran Nicholson, Joanne Dunne, Peter DaBell, Alexander Beaton Garcia, Andrew D. Bage, Jamie H. Docherty, Thomas A. Hunt, Thomas Langer, Stephen P. Thomas
Summary: A turnover strategy using boron-oxygen transborylation has been developed to transform stoichiometric borane reagents into catalysts for the enantioselective reduction of ketones, including biologically active molecules and those with reducible groups.
Article
Chemistry, Organic
Lili Chen, Senmiao Xu
Summary: Alkylboronic acids are widely used in various fields, and the transition-metal-catalyzed hydroboration of alkenes is a convenient method for their synthesis. However, achieving selective hydroboration of heteroatom-substituted alkenes and regioselective hydroboration of aliphatic internal alkenes remains a challenge. This account highlights recent advancements in ligand-enabled transition-metal-catalyzed regio- and/or stereoselective hydroboration of alkenes.
Article
Chemistry, Multidisciplinary
Andre U. Augustin, Sergio Di Silvio, Ilan Marek
Summary: Here, we demonstrate a method to form acyclic frameworks with two consecutive stereocenters of either tertiary or quaternary nature starting from easily accessible cyclopropenes. This approach involves regio-and diastereoselective hydro or carboborylation of substituted cyclopropenyl esters. Formation of boronate complexes by adding nucleophiles and subsequent stereospecific 1,2-migration with carbon-carbon bond cleavage delivers the desired compounds.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)