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| http://dx.doi.org/10.15227/orgsyn.093.0228 | DOI Listing |
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Asymmetric Radical Oxyboration of β-Substituted Styrenes via Late-Stage Stereomutation.
Angew Chem Int Ed Engl
November 2023
Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of Chemistry, Northeast Normal University, Changchun, 130024, China.
Herein, we report an unprecedented copper-catalyzed highly enantio- and diastereoselective radical oxyboration of β-substituted styrenes. The lynchpin of success is ascribed to the development of a late-stage stereomutation strategy, which enables enantioenriched cis-isomers among a couple of early-generated diastereomers to be converted into trans-isomer counterparts, thus fulfilling high diastereocontrol; while the degree of enantio-differentiation is determined by the borocupration process of the C=C bond. This reaction provides an efficient protocol to access enantioenriched trans-1,2- dioxygenation products.
View Article and Find Full Text PDFDirect Synthesis of Alkenylboronates from Alkenes and Pinacol Diboron via Copper Catalysis.
Org Lett
January 2019
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering , Shanghai Jiao Tong University, 800 Dongchuan Road , Shanghai , 200240 , China.
We report an efficient approach for the direct synthesis of alkenylboronates using copper catalysis. The Cu/TEMPO catalyst system (where TEMPO = (2,2,6,6-tetramethylpiperidin-1-yl)oxyl) exhibits both excellent reactivity and selectivity for the synthesis of alkenylboronates, starting from inexpensive and abundant alkenes and pinacol diboron. This approach allows for the direct functionalization of both aromatic and aliphatic terminal alkenes.
View Article and Find Full Text PDFSelective oxymetalation of terminal alkynes 6- cyclization: mechanistic investigation and application to the efficient synthesis of 4-substituted isocoumarins.
Chem Sci
July 2018
Department of Applied Chemistry , Graduate School of Engineering , Osaka University, 2-1 Yamadaoka, Suita , Osaka 565-0871 , Japan . Email:
The cyclization of heteroatom-containing alkynes with π acidic metal salts is an attractive method to prepare heterocycles because the starting materials are readily available and the organometallic compounds are useful synthetic intermediates. A new organometallic species in the heterocyclization provides an opportunity to synthesize heterocycles that are difficult to obtain. Herein, we describe a novel cyclic oxymetalation of 2-alkynylbenzoate with indium or gallium salts that proceeds with an unusual regioselectivity to give isocoumarins bearing a carbon-metal bond at the 4-position.
View Article and Find Full Text PDFBoron-Heteroatom Addition Reactions via Borylative Heterocyclization: Oxyboration, Aminoboration, and Thioboration.
Acc Chem Res
October 2017
Department of Chemistry, University of California, Irvine, California 92697-2025, United States.
Organoboron compounds and heterocycles are powerful building blocks and precursors for organic synthesis, including for drug discovery and agrochemical and material synthesis. The common strategy for the synthesis of borylated heterocycles involves two separate synthetic steps: first, synthesis of the heterocyclic core, and second, borylation of the core through established methods such as transition-metal-catalyzed C-H or C-X activation/borylation or lithiation/borylation. In this Account, we describe our laboratory's development of borylative heterocyclization reactions that access the heterocyclic core and install boron in one synthetic step.
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Organometallics
March 2016
Department of Chemistry, University of California, Irvine, California 92697-2025, United States.
In the present study, the oxyboration reaction catalyzed by IPrAuTFA in the presence and absence of NaTFA has been examined with kinetic studies, mass spectrometry, and H NMR and B NMR spectroscopy. Data from monitoring the reactions over the temperature range from 30 to 70 °C, the catalyst range from 1.3 to 7.
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