- Visible Light Induced Rhodium(I)-Catalyzed C?H Borylation
-
An efficient visible light induced rhodium(I)-catalyzed regioselective borylation of aromatic C?H bonds is reported. The photocatalytic system is based on a single NHC?RhI complex capable of both harvesting visible light and enabling the bond breaking/forming at room temperature. The chelating nature of the NHC-carboxylate ligand was critical to ensure the stability of the RhI complex and to provide excellent photocatalytic activities. Experimental mechanistic studies evidenced a photooxidative ortho C?H bond addition upon irradiation with blue LEDs, leading to a cyclometalated RhIII-hydride intermediate.
- Thongpaen, Jompol,Manguin, Romane,Dorcet, Vincent,Vives, Thomas,Duhayon, Carine,Mauduit, Marc,Baslé, Olivier
-
supporting information
p. 15244 - 15248
(2019/10/22)
-
- Directed: Ortho C-H borylation catalyzed using Cp?Rh(iii)-NHC complexes
-
Cp?Rh(NHC) complexes with bulky chiral bidentate NHC-carboxylate ligands were efficiently synthesized and fully characterized including solid-state structures. These unprecedented rhodium(iii) complexes demonstrated high selectivity in pyridine-directed ortho-C-H borylation of arenes under mild conditions.
- Thongpaen, Jompol,Schmid, Thibault E.,Toupet, Loic,Dorcet, Vincent,Mauduit, Marc,Baslé, Olivier
-
supporting information
p. 8202 - 8205
(2018/07/29)
-
- Aerobic Direct C(sp2)-H Hydroxylation of 2-Arylpyridines by Palladium Catalysis Induced with Aldehyde Auto-Oxidation
-
Herein we present a Pd-catalyzed direct C-H hydroxylation of 2-arylpyridines using molecular oxygen (O2) as the sole oxidant. The key aspects of the method include: (a) the activation of molecular oxygen with a nontoxic and inexpensive aldehyde
- Das, Prasenjit,Saha, Debajyoti,Saha, Dibyajyoti,Guin, Joyram
-
p. 6050 - 6054
(2016/09/09)
-
- Direct ortho-Hydroxylation of 2-Phenylpyridines using Palladium(II) Chloride and Hydrogen Peroxide
-
Direct functionalization of the ubiquitous C-H bond is receiving much attention because complex structures can be formed from simple precursors. This paper reports a useful method for the direct hydroxylation of 2-phenylpyridines using palladium(II) chloride and aqueous hydrogen peroxide. In this method, hydrogen peroxide, which has high atom efficiency, is employed as the oxidant and phenol derivatives are generated via C-H activation.
- Yamaguchi, Tomoaki,Yamaguchi, Eiji,Tada, Norihiro,Itoh, Akichika
-
supporting information
p. 2017 - 2021
(2015/06/23)
-
- Synthesis of Chemically and Configurationally Stable Monofluoro Acylboronates: Effect of Ligand Structure on their Formation, Properties, and Reactivities
-
The recent disclosures of two classes of acylborons, potassium acyltrifluoroborates (KATs) and N-methyliminodiacetyl (MIDA) acylboronates, demonstrated that certain acylboron species can be both remarkably stable and uniquely reactive. Here we report new classes of ligands for acylboronates that have a significant influence on the formation, properties, and reactivities of acylboronates. Our systematic investigations identified a class of neutral, monofluoroboronates that can be prepared in a one step, gram-scale fashion from readily accessible KATs. These monofluoroboronates are stable to air, moisture, and silica gel chromatography and can be easily handled without any special precautions. X-ray crystallography, NMR spectroscopy, and HPLC studies showed that they are tetravalent, configurationally stable B-chiral acylboronates. Significantly, the ligands on the boronate allow for fine-tuning of the properties and reactivity of acylboronates. In amide-forming ligation with hydroxylamines under aqueous conditions, a considerable difference in reactivity was observed as a function of ligand structure. The solid-state structures suggested that subtle steric and conformational factors modulate the reactivities of the acylboronates.
- Noda, Hidetoshi,Bode, Jeffrey W.
-
p. 3958 - 3966
(2015/04/14)
-
- PdCl2 and N-hydroxyphthalimide co-catalyzed c sp 2 -H hydroxylation by dioxygen activation
-
Rad transition: The combination of transition-metal-catalyzed C-H activation and a NHPI-initiated radical process is essential for the title transformation. The neutral conditions and the ideal oxidant, molecular oxygen, make this hydroxylation environmen
- Yan, Yuepeng,Feng, Peng,Zheng, Qing-Zhong,Liang, Yu-Feng,Lu, Jing-Fen,Cui, Yuxin,Jiao, Ning
-
supporting information
p. 5827 - 5831
(2013/06/27)
-
- Regioselective synthesis of 2-(2-hydroxyaryl)pyridines from the reactions of benzynes with pyridine N-oxides
-
By modifying the conditions from those in Larock's reported synthesis of 3-(2-hydroxyaryl)pyridines from benzynes, and pyridine N-oxides, we altered the regioselectivity of the reaction toward an efficient synthesis of 2-substituted pyridines. The presenc
- Shaibu, Balagopal S.,Kawade, Rahul Kisan,Liu, Rai-Shung
-
p. 6834 - 6839
(2012/11/07)
-
- α1-Adrenoceptor agonists: The identification of novel α1A subtype selective 2′-heteroaryl-2-(phenoxymethyl)imidazolines
-
Novel 2′-heteroaryl-2-(phenoxymethyl)imidazolines have been identified as potent agonists of the cloned human α1-adrenoceptors in vitro. The nature of the 2′-heteroaryl group can have significant effects on the potency, efficacy, and subtype selectivity in this series. α1A Subtype selective agonists have been identified.
- Bishop, Michael J.,Barvian, Kevin A.,Berman, Judd,Bigham, Eric C.,Garrison, Deanna T.,Gobel, Michael J.,Hodson, Stephen J.,Irving, Paul E.,Liacos, James A.,Navas, Iii, Frank,Saussy Jr., David L.,Speake, Jason D.
-
p. 471 - 475
(2007/10/03)
-