19202-21-2Relevant academic research and scientific papers
1,2-Asymmetric induction in the addition of XCCl3 to trans-cinnamoyl-N-pyrrolidine
Gasanov, R. G.,Videnskaya, S. O.,Il'inskaya, L. V.,Belokon', Yu. N.
, p. 1688 - 1690 (1994)
In the reaction of XCCl3 (X = Br (1), Cl (2)) with trans-PhCH=CHC(O)Y (Y = N-pyrrolidinyl) (3) in the presence of Fe(CO)5 as the catalyst (or benzoyl peroxide in the case of 1) at 80 deg C, the addition of CCl3 radicals occurs regioselectively at the α-ca
Phytotoxicity of sarmentine isolated from long pepper (Piper longum) fruit
Huang, Huazhang,Morgan, Christy M.,Asolkar, Ratnakar N.,Koivunen, Marja E.,Marrone, Pamela G.
, p. 9994 - 10000 (2010)
Discovery of novel natural herbicides has become crucial to overcome increasing weed resistance and environmental issues. In this article, we describe the finding that a methanol extract of dry long pepper (Piper longum L.) fruits is phytotoxic to lettuce (Lactuca sativa L.) seedlings. The bioassay-guided fractionation and purification of the crude extract led to isolation of sarmentine (1), a known compound, as the active principle. Phytotoxicity of 1 was examined with a variety of seedlings of field crops and weeds. Results indicated that 1 was a contact herbicide and possessed broad-spectrum herbicidal activity. Moreover, a series of sarmentine analogues were then synthesized to study the structure-activity relationship (SAR). SAR studies suggested that phytotoxicity of sarmentine and its analogues was specific due to chemical structures, i.e., the analogues of the acid moiety of 1 were active, but the amine and its analogues were inactive; the ester analogues and amide analogues with a primary amine of 1 were also inactive. In addition, quantification of 1 from different resources of the dry P. longum fruits using liquid chromatography-mass spectrometry showed a wide variation, ranging from almost zero to 0.57%. This study suggests that 1 has potential as an active lead molecule for synthesized herbicides as well as for bioherbicides derived from natural resources.
Photoenzymatic Reductions Enabled by Direct Excitation of Flavin-Dependent "Ene"-Reductases
Sandoval, Braddock A.,Clayman, Phillip D.,Oblinsky, Daniel G.,Oh, Seokjoon,Nakano, Yuji,Bird, Matthew,Scholes, Gregory D.,Hyster, Todd K.
supporting information, p. 1735 - 1739 (2021/01/25)
Non-natural photoenzymatic reactions reported to date have depended on the excitation of electron donor-acceptor complexes formed between substrates and cofactors within protein active sites to facilitate electron transfer. While this mechanism has unlocked new reactivity, it limits the types of substrates that can be involved in this area of catalysis. Here we demonstrate that direct excitation of flavin hydroquinone within "ene"-reductase active sites enables new substrates to participate in photoenzymatic reactions. We found that by using photoexcitation these enzymes gain the ability to reduce acrylamides through a single electron transfer mechanism.
Erratum: Photoenzymatic Reductions Enabled by Direct Excitation of Flavin-Dependent 'Ene'-Reductases (J. Am. Chem. Soc. (2021) 143:4 (1735-1739) DOI: 10.1021/jacs.0c11494)
Sandoval, Braddock A.,Clayman, Phillip D.,Oblinsky, Daniel G.,Oh, Seokjoon,Nakano, Yuji,Bird, Matthew,Scholes, Gregory D.,Hyster, Todd K.
supporting information, p. 3662 - 3662 (2021/04/09)
Support by the Department of Energy was inadvertently left out of the Acknowledgments and a coauthor's name was misspelled in the Supporting Information. The scientific part of the manuscript remains unchanged. The complete correct Acknowledgment paragraph is as follows.
Photocatalytic aldehydes/alcohols/toluenes oxidative amidation over bifunctional Pd/MOFs: Effect of Fe-O clusters and Lewis acid sites
Bian, Fengxia,Cheng, Hongmei,Jiang, Heyan,Sun, Bin,Tan, Jiangwei,Zang, Cuicui
, p. 279 - 287 (2021/08/21)
Heterogeneous photocatalytic organic synthesis is fascinating because of the utilization of ubiquitous solar light for chemical transformations. Here, three Fe-MOFs with different Fe-O clusters, Lewis acid sites and morphologies were synthesized through coordination structure engineering. Pd/Fe-MOFs nanocomposites were used to challenge the amide bond green synthesis with visible light. Pd/MIL-101(Fe) exhibited the best photocatalytic performance due to the easily excited Fe3-μ3-oxo clusters for light absorption, the efficient photogenerated carriers separation and migration, the large amount of Lewis acid sites based aldehydes and amines condensation promotion and the efficient O2 reduction to superoxide radicals over photogenerated electron-rich Pd NPs. Various aldehydes, alcohols and toluenes could be transformed to amide compounds with amines over Pd/MIL-101(Fe) with just oxygen or air as the green oxidant and water as the by-product. One-pot C–C cross-coupling and photo-redox C–N coupling cascade reactions could also be achieved over Pd/MIL-101(Fe). This work shed light on the efficient and sustainable amide bonds synthesis.
Stereoselective formal hydroamidation of si-substituted arylacetylenes with DIBAL-H and isocyanates: Synthesis of (E)- And (Z)-α-Silyl-α,β-unsaturated amides
Lee, Yunmi,Jung, Byunghyuck,Lee, Hanseul,Cho, Soohong
, p. 12024 - 12035 (2020/11/10)
An efficient and stereoselective method for the synthesis of (E)- and (Z)-α-silyl-α,β-unsaturated amides and its synthetic applications are presented herein. The solvent-controlled hydroaluminations of Si-substituted alkynes with DIBAL-H generate diastereomerically enriched alkenylaluminum reagents that are directly reacted with isocyanates at ambient temperature to afford α-silyl-α,β-unsaturated amides in high yields with retained stereoselectivity. In particular, this process enables the synthesis of a broad range of (E)-α-silyl-α,β- unsaturated amides, which are the less studied isomers. The synthetic utility of this method is highlighted by its short reaction time, ease of purification, easily accessible substrates and reagents, gram-scale synthesis, and the further transformations of C-Si bonds into C-H, C-X, and C-C bonds.
Rapid access to cinnamamides and piper amides: Via three component coupling of arylaldehydes, amines, and Meldrum's acid
Ghosh, Santanu,Jana, Chandan K.
supporting information, p. 5803 - 5807 (2019/11/11)
A practical method for the synthesis of cinnamamides and piper amides via a conceptually novel three component reaction of aldehydes, amines and Meldrum's acid has been reported. The reaction proceeds under operationally simple conditions without the aid of coupling reagents, oxidants, or catalysts, which are essential for the preparation of cinnamamides/piper amides via known methods. The formation of undesired chemical wastes that generally originate from the use of coupling reagents, oxidants, or catalysts has been avoided to make this reaction more atom economical.
Enhancing Ligand-Free Fe-Catalyzed Aminocarbonylation of Alkynes by ZrF4
Huang, Zijun,Dong, Yanan,Li, Yudong,Makha, Mohamed,Li, Yuehui
, p. 5236 - 5240 (2019/09/03)
Zirconium fluoride was utilized to promote efficiently iron-catalyzed aminocarbonylation between alkynes and amines without the use of extra ligands. In particular, this new system is applicable to a wide range of amine and alkyne substrates affording α,β-unsaturated amides in good to excellent yields. Preliminary mechanistic studies reveal the activation model involving interactions of ZF4 with both iron catalyst and amine substrates.
Radical α,β-Dehydrogenation of Saturated Amides via α-Oxidation with TEMPO under Transition Metal-Free Conditions
Wang, Mei-Mei,Sui, Guo-Hui,Cui, Xian-Chao,Wang, Hui,Qu, Jian-Ping,Kang, Yan-Biao
, p. 8267 - 8274 (2019/06/27)
A transition metal-free radical process for the selective α,β-dehydrogenation of saturated amides under mild conditions is developed. Utilizing radical activation strategy, the challenging issue associated with the low α-acidity of amides is resolved. For the first time, α,β-unsaturated Weinreb amides and acrylamides could be efficiently prepared directly from corresponding saturated amides. Mechanistic studies confirm the radical nature of this transformation. Two gram scale α,β-dehydrogenation have also been performed to demonstrate the utility of this method.
Visible-light-promoted oxidation/condensation of benzyl alcohols with dialkylacetamides to cinnamides
Yang, Tianlong,Lu, Maojian,Lin, Zhaowei,Huang, Mingqiang,Cai, Shunyou
supporting information, p. 449 - 453 (2019/01/24)
Oxidative cross-coupling reactions of benzyl alcohols with N,N-dialkylacetamides were developed only employing oxygen as the terminal oxidant, efficiently providing a new, novel protocol for the construction of multifunctionalized cinnamides with the synergistic effects of KOH, organic photocatalyst eosin Y, and visible light irradiation at room temperature. A broad substrate scope and mild reaction conditions are the prominent features of this transformation.
