The gram-scale polymerization of a novel azaborine vinyl monomer is reported. We describe an efficient and high-yielding synthesis of B-vinyl-2,1-borazanaphthalene. Homopolymers and co-polymers with 2-vinylnaphthalene are characterized by heteronuclear NMR and absorbance spectroscopy.
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http://dx.doi.org/10.1039/c7cc02300f | DOI Listing |
Nat Commun
November 2024
Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry at Fuzhou University, Fuzhou, Fujian, 350108, China.
The catalytic asymmetric synthesis of axially chiral alkenes remains a daunting challenge due to the lower rotational barrier, especially for longer stereogenic axis (e.g. C-B axis).
View Article and Find Full Text PDFOrg Lett
August 2024
Department of Chemistry, Texas A&M University, College Station, Texas 77843, United States.
In contrast to transition-metal-catalyzed difunctionalization of activated alkenes, selective alkylarylation of vinyl azaarenes is underdeveloped. Consequently, the lack of modular and rapid syntheses of 1,1-bis(hetero)arylalkanes limits their exploration in medicinal chemistry. Herein we report a protocol using commercially available iron salts, bisphosphine ligands, fluoroalkyl halides, and Grignard reagents that enables the selective 1,2-fluoroalkyl(hetero)arylation of vinyl azaarenes.
View Article and Find Full Text PDFChem Soc Rev
February 2024
Department of Chemistry, Boston College, Chestnut Hill, Massachusetts, 02467-3860, USA.
Borataalkenes and boraalkenes are the boron-containing isoelectronic analogues of alkenes and vinyl cations respectively. Compared with alkenes, the borataalkene and boraalkene ligand motifs in transition metal coordination chemistry are relatively underexplored. In this review, the synthesis of borataalkene and boraalkene complexes and other transition metal complexes featuring the η-B,C coordination mode is described.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
February 2022
Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology, 4259 Nagatsuta-cho Midori-ku, Yokohama, 226-8503, Japan.
A palladium-catalyzed N-H/B-H double activation of 1,2-dihydro-1,2-benzazaborines proceeded via cycloaddition with vinyl ethylene carbonate to produce polycyclic oxazaborolidines in 31-96 % yield. The key step in this process is the release of molecular hydrogen from a borate intermediate. Using a SPINOL-derived phosphoramidite as a chiral ligand, chiral oxazaborolidines were synthesized in good to high yields with excellent enantioselectivity (up to 95 % ee).
View Article and Find Full Text PDFChem Commun (Camb)
June 2017
Department of Chemistry, Johns Hopkins University, 3400 N. Charles St, Baltimore, MD 21218, USA.
The gram-scale polymerization of a novel azaborine vinyl monomer is reported. We describe an efficient and high-yielding synthesis of B-vinyl-2,1-borazanaphthalene. Homopolymers and co-polymers with 2-vinylnaphthalene are characterized by heteronuclear NMR and absorbance spectroscopy.
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