62924-93-0Relevant academic research and scientific papers
Nickel-Catalyzed Hydrodeoxygenation of Aryl Sulfamates with Alcohols as Mild Reducing Agents
Matsuo, Kasumi,Kuriyama, Masami,Yamamoto, Kosuke,Demizu, Yosuke,Nishida, Koyo,Onomura, Osamu
, p. 4449 - 4460 (2021/08/25)
The nickel-catalyzed hydrodeoxygenation of aryl sulfamates has been developed with alcohols as mild reductants. A variety of functional groups and heterocycles were tolerated in this reaction system to give the desired products in high yields. In addition, the gram-scale process and stepwise cine-substitution were also achieved with high efficiency.
Directed ortho and Remote Metalation–Suzuki–Miyaura Cross Coupling Route to Azafluorenol Core Liquid Crystals
Lai, Ping-Shan,Jansen-Van Vuuren, Ross D.,Lemieux, Robert P.,Snieckus, Victor
, p. 17543 - 17549 (2021/12/13)
Two new smectic C* mesogens containing a hexyloxy side chain and an azafluorenone (3a) or azafluorenol (3b) core were synthesized using a combined directed ortho metalation-directed remote metalation–Suzuki–Miyaura cross-coupling strategy. 3b was formed i
Synthetic Studies of the Rubellin Natural Products: Development of a Stereoselective Strategy and Total Synthesis of (+)-Rubellin C
Gartman, Jackson A.,Tambar, Uttam K.
, p. 11237 - 11262 (2021/08/16)
This manuscript describes our studies of the class of natural products known as the rubellins, culminating in the total synthesis of (+)-rubellin C. These anthraquinone-based natural products contain a variety of stereochemical and architectural motifs, including a 6-5-6-fused ring system, 5 stereogenic centers, and a central quaternary center. Herein, we report our development of a strategy to target the stereochemically dense core and anthraquinone nucleus, including approaches such as a bifunctional allylboron and vinyl triflate reagent, an anthraquinone benzylic metalation strategy, and a late-stage anthraquinone introduction strategy. Our studies culminate in a successful route to highly functionalized anthraquinone-based natural product scaffolds and a stereoselective total synthesis of (+)-rubellin C. These strategies and outcomes will aid in synthetic planning toward anthraquinone-based natural products of high interest.
Total Synthesis of (+)-Rubellin C
Gartman, Jackson A.,Tambar, Uttam K.
, p. 9145 - 9150 (2020/08/24)
The rubellins are a family of stereochemically complex anthraquinoid heterodimers containing an unprecedented chemical scaffold. Although the rubellins have been known for over three decades, no total synthesis has been achieved since their discovery. The
HMF and furfural: Promising platform molecules in rhodium-catalyzed carbonylation reactions for the synthesis of furfuryl esters and tertiary amides
Qi, Xinxin,Zhou, Rong,Ai, Han-Jun,Wu, Xiao-Feng
, p. 215 - 221 (2019/11/25)
A biomass involved rhodium-catalyzed carbonylative synthesis of furfuryl esters and tertiary amides has been developed. 5-Hydroxymethylfurfural (HMF) was used as both substrate and CO surrogate for the first time in a carbonylation reaction, and both alkyl and aryl iodides were tolerated well to afford the desired furfuryl esters in moderate to good yields. In addition, furfural was also utilized as a CO source for the synthesis of tertiary amides. A variety of tertiary amides were obtained in moderate to excellent yields with good functional groups compatibility. Notably, tertiary amines were used as the amine source through a C[sbnd]N bond cleavage pathway in the absence of additional oxidant.
Amide-Directed Ru-Catalyzed Hydrodemethoxylation of ortho-Methoxy-Benzamides and -Naphthamides: A D oM Reaction Counterpart
Zhao, Yigang,Snieckus, Victor
supporting information, p. 2826 - 2830 (2018/05/29)
A new ruthenium-catalyzed hydrodemethoxylation of ortho-methoxy-benzamides and -naphthamides involving amide-directed C-OMe bond activation and hydride reduction is disclosed. The reaction is general, proceeding under RuH2(CO)(PPh3)3 catalysis using either triethylsilane (Et3SiH) or diisobutylaluminum hydride (DIBAL-H) as the reductant. The corresponding C-N hydrodeamination reaction is also briefly reported.
Chirality controlled responsive self-assembled nanotubes in water
Van Dijken,?tacko,Stuart,Browne,Feringa
, p. 1783 - 1789 (2017/03/09)
The concept of using chirality to dictate dimensions and to store chiral information in self-assembled nanotubes in a fully controlled manner is presented. We report a photoresponsive amphiphile that co-assembles with its chiral counterpart to form nanotu
Amphiphilic Molecular Motors for Responsive Aggregation in Water
Van Dijken, Derk Jan,Chen, Jiawen,Stuart, Marc C. A.,Hou, Lili,Feringa, Ben L.
supporting information, p. 660 - 669 (2016/02/05)
The novel concept of amphiphilic molecular motors that self-assemble into responsive supramolecular nanotubes in water is presented. The dynamic function of the molecular motor units inside the supramolecular assemblies was studied using UV-vis absorption
Directed Metalation-Suzuki-Miyaura Cross-Coupling Strategies: Regioselective Synthesis of Hydroxylated 1-Methyl-phenanthrenes
J?rgensen, K?re B.,Rantanen, Toni,D?rfler, Thilo,Snieckus, Victor
, p. 9410 - 9424 (2015/10/12)
A general, efficient, and regioselective synthesis of a series of hydroxylated 1-methylphenanthrenes 9 by a combined directed ortho metalation (DoM)-Suzuki-Miyaura cross-coupling-directed remote metalation (DreM) sequence is reported. Diversity to this methodology was achieved by a regioselective DoM rather than DreM reaction, affording more highly substituted phenanthrols (Table 2). Application of the turbo-Grignard reagent (i-PrMgCl·LiCl) in the Ni-catalyzed Corriu-Kumada reaction gave efficient decarbamoylation (Tables 3and 4). Additional features are the TMS protecting group and halo-induced ipso-desilylation tactics applied to the regioselective synthesis of phenanthrenes (Scheme 2).
NHC-Pd complex-catalyzed double carbonylation of aryl iodides with secondary amines to α-keto amides
Zheng, Shuzhan,Wang, Yan,Zhang, Chunyan,Liu, Jianhua,Xia, Chungu
, p. 48 - 53 (2014/01/06)
A series of palladium-NHC compounds were prepared and their catalytic activity in the double carbonylation of aryl iodides to synthesize α-keto amides were examined. Palladium complexes bearing mixed NHC-phosphine exhibited high efficiency for the double carbonylation reaction. The effects of different solvents, base, temperature, carbon monoxide (CO), pressure, various amine and aryl iodides were investigated. Both electron-rich and electron-deficient aryl iodides afforded the corresponding substituted α-keto amides in moderate to good yields. A possible mechanism was also proposed. Copyright
