76-09-5Relevant articles and documents
Reductive coupling of phthalic anhydrides with aliphatic ketones by low-valent titanium: Unusual two-to-one coupling for preparation of 3,3-disubstituted phthalides
Kise, Naoki,Yamamoto, Shota,Sakurai, Toshihiko
, (2020)
The reductive coupling of phthalic anhydrides with acetone by Zn-TiCl4 in THF gave two-to-one and one-to-one coupled products. The coupled products were transformed to 3,3-diisopropyl-, 3-isopropylidene-, and 3-isopropylphthalides. In addition, the reductive coupling of phthalic anhydrides with acetonylacetone by Zn-TiCl4 in THF gave 3-spirocyclopentanylphtalides stereoselectively.
Duran et al.
, p. 442 (1977)
Synthesis of Layered Carbonitrides from Biotic Molecules for Photoredox Transformations
Yang, Can,Wang, Bo,Zhang, Linzhu,Yin, Ling,Wang, Xinchen
, p. 6627 - 6631 (2017)
The construction of layered covalent carbon nitride polymers based on tri-s-triazine units has been achieved by using nucleobases (adenine, guanine, cytosine, thymine and uracil) and urea to establish a two-dimensional semiconducting structure that allows band-gap engineering applications. This biomolecule-derived binary carbon nitride polymer enables the generation of energized charge carrier with light-irradiation to induce photoredox reactions for stable hydrogen production and heterogeneous organosynthesis of C?O, C?C, C?N and N?N bonds, which may enrich discussion on chemical reactions in prebiotic conditions by taking account of the photoredox function of conjugated carbonitride semiconductors that have long been considered to be stable HCN-derived organic macromolecules in space.
Protodeboronation of (Hetero)Arylboronic Esters: Direct versus Prehydrolytic Pathways and Self-/Auto-Catalysis
Hayes, Hannah L. D.,Wei, Ran,Assante, Michele,Geogheghan, Katherine J.,Jin, Na,Tomasi, Simone,Noonan, Gary,Leach, Andrew G.,Lloyd-Jones, Guy C.
supporting information, p. 14814 - 14826 (2021/09/13)
The kinetics and mechanism of the base-catalyzed hydrolysis (ArB(OR)2→ ArB(OH)2) and protodeboronation (ArB(OR)2→ ArH) of a series of boronic esters, encompassing eight different polyols and 10 polyfluoroaryl and heteroaryl moieties, have been investigated by in situ and stopped-flow NMR spectroscopy (19F,1H, and11B), pH-rate dependence, isotope entrainment,2H KIEs, and KS-DFT computations. The study reveals the phenomenological stability of boronic esters under basic aqueous-organic conditions to be highly nuanced. In contrast to common assumption, esterification does not necessarily impart greater stability compared to the corresponding boronic acid. Moreover, hydrolysis of the ester to the boronic acid can be a dominant component of the overall protodeboronation process, augmented by self-, auto-, and oxidative (phenolic) catalysis when the pH is close to the pKaof the boronic acid/ester.
GaN nanowires as a reusable photoredox catalyst for radical coupling of carbonyl under blacklight irradiation
Botton, Gianluigi,Cen, Yunen,Cheng, Shaobo,Li, Chao-Jun,Liu, Mingxin,Mi, Zetian,Rashid, Roksana T.,Tan, Lida
, p. 7864 - 7870 (2020/08/19)
Employing photo-energy to drive the desired chemical transformation has been a long pursued subject. The development of homogeneous photoredox catalysts in radical coupling reactions has been truly phenomenal, however, with apparent disadvantages such as the difficulty in separating the catalyst and the frequent requirement of scarce noble metals. We therefore envisioned the use of a hyper-stable III-V photosensitizing semiconductor with a tunable Fermi level and energy band as a readily isolable and recyclable heterogeneous photoredox catalyst for radical coupling reactions. Using the carbonyl coupling reaction as a proof-of-concept, herein, we report a photo-pinacol coupling reaction catalyzed by GaN nanowires under ambient light at room temperature with methanol as a solvent and sacrificial reagent. By simply tuning the dopant, the GaN nanowire shows significantly enhanced electronic properties. The catalyst showed excellent stability, reusability and functional tolerance. All reactions could be accomplished with a single piece of nanowire on Si-wafer. This journal is