60460-70-0

Upstream product

• 106-41-2 4-bromo-phenol 
• 7529-22-8 4-methylmorpholine N-oxide 
• 110-91-8 morpholine 
• 50-00-0 formaldehyd 
• 5467-74-3 4-Bromophenylboronic acid 

Downstream Products

• 7016-14-0 N-(5-bromo-2-methoxybenzyl)morpholine 

Relevant academic research and scientific papers

Acetyl Acetone Covalent Triazine Framework: An Efficient Carbon Capture and Storage Material and a Highly Stable Heterogeneous Catalyst

We present, for the first time, Covalent Triazine Frameworks functionalized with acetyl acetonate group (acac-CTFs). They are obtained from the polymerization of 4,4'-malonyldibenzonitrile under ionothermal conditions and exhibit BET surface areas up to 1626 m2/g. The materials show excellent CO2 uptake (3.30 mmol/g at 273 K and 1 bar), H2 storage capacity (1.53 wt% at 77 K and 1 bar) and a good CO2/N2 selectivity (up to 46 at 298 K). The enhanced CO2 uptake value and good selectivity are due to the presence of dual polar sites (N and O) throughout the material. In addition, acac-CTF was used to anchor VO(acac)2 as a heterogeneous catalyst. The V@acacCTF showed outstanding reactivity and reusability for the modified Mannich-type reaction with a higher turnover number than the homogeneous catalyst. The higher reactivity and reusability of the catalyst comes from the coordination of the vanadyl ions to the acetyl acetonate groups present in the material. The strong metalation is confirmed from Fourier Transform Infrared analysis, 13C MAS NMR spectral analysis and X-ray photoelectron spectroscopy measurement. Detailed characterization of the V@acac-CTF reveals that electron donation from O^O of the acetyl acetonate group to VO(acac)2, combined with the very high surface area of acac-CTF, is responsible for the stabilization of the catalyst. Overall, this contribution highlights the necessity of stable catalytic binding sites on heterogeneous supports to fabricate greener catalysts for sustainable chemistry.

The modified-Mannich reaction: Conversion of arylboronic acids and subsequent coupling with paraformaldehyde and amines toward the one-pot synthesis of Mannich bases and benzoxazines

A modified Mannich reaction has been developed for the synthesis of Mannich bases and benzoxazines via the oxidative hydroxylation of arylboronic acids and subsequent coupling with paraformaldehyde and amines in one pot. This modified Mannich reaction is easily carried out to afford the target products in good to excellent yields and tolerates a variety of functional groups.

Cu(II)-Catalyzed ortho-Selective Aminomethylation of Phenols

A Cu(II)-catalyzed ortho-selective functionalization of free phenols with trifluoroborates to afford Csp2-Csp3 coupling products under mild conditions has been developed. A variety of functional groups on the phenol and the potassium aminomethyltrifluoroborate substrates were found compatible, furnishing the corresponding products in moderate to excellent yields. A single-electron transfer radical coupling mechanism involving a six-membered transition state is proposed to rationalize the high levels of ortho-selectivity in the reaction. This protocol provides straightforward access to ortho-aminomethyl-substituted phenols, unnatural amino acids and other bioactive small molecules.

A modified Mannich-Type reaction catalyzed by VO(acac)2

(Equation Presented) A fackile VO(acac)2-catalyzed in situ generation of iminium ions from amine N-oxides and their participation in a modified Mannich-type reaction is described.