Article
Chemistry, Organic
Jiao-Mei Wang, Teng Chen, Chang-Sheng Yao, Kai Zhang
Summary: Herein, an NHC (N-heterocyclic carbene)-catalyzed radical coupling reaction between aldehydes and azobis(isobutyronitrile) (AIBN) has been developed, providing an efficient and convenient approach for the synthesis of fi-ketonitriles containing a quaternary carbon center (31 examples, up to >99% yield) utilizing commercially available substrates. This protocol features broad substrate scope, good functional group tolerance, and high efficiency under metal-free and mild reaction conditions.
Article
Chemistry, Organic
Kensuke Kiyokawa, Ikumi Noguchi, Takaya Nagata, Satoshi Minakata
Summary: In this study, we present a bromocyanation reaction of styrene derivatives using cyanogen bromide in the presence of tris(pentafluorophenyl)borane as a Lewis acid catalyst. The reaction proceeds through a stereospecific syn-addition and provides a straightforward approach to beta-bromonitriles.
Article
Chemistry, Applied
Yu-ki Sugiyama, Masaki Amo, Kouta Ibe, Sentaro Okamoto
Summary: The reactivity of nitriles in a CoCl2-6H(2)O/dppe/Zn-catalyzed diyne-nitrile cycloaddition was studied. It was found that cyanamides are good substrates and result in the formation of 2-aminopyridines. Notably, N-unsubstituted cyanamide (H2N-CN) can react with 1,6-diynes to produce N-unsubstituted 2-aminopyridines, which cannot be obtained through other catalytic reactions and serve as versatile intermediates for further transformations.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Fang Xie, Jie Zhao, Deyue Ren, Jianming Xue, Jingyi Wang, Qin Zhao, Lu Liu, Xiaodan Liu
Summary: A Cu-catalyzed coupling reaction between cyclic imino esters and 2H-azirines has been developed, allowing for the synthesis of novel optically active aziridines in high yields and with excellent levels of diastereo- and enantioselectivities under mild conditions. This method features a broad substrate scope, good functional group compatibility, and enriches the existing reaction type for the rapid synthesis of optically active aziridines bearing vicinal tetrasubstituted stereogenic carbon centers.
Article
Chemistry, Multidisciplinary
Kieran Benn, Kieran Nicholson, Thomas Langer, Stephen P. Thomas
Summary: Cyanation serves as a simple method for introducing nitrile group into organic molecules and installing various functional groups through transition metal catalysis and hydrogen cyanide gas. Electrophilic cyanation of enones can be achieved using main-group catalyst and non-toxic cyanide source, with a broad substrate scope including reducible functional groups. Mechanistic studies suggest an amino-borane intermediate undergoing B-N transborylation for catalytic turnover.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Guodong Zhang, Chengyu Zhang, Ye Tian, Feng Chen
Summary: In this study, a concise and efficient method for the synthesis of diverse nitrile compounds from ubiquitous carboxylic acids was achieved using an inexpensive iron catalyst. The method demonstrated compatibility with primary, secondary, tertiary, and aryl carboxylic acids, as well as various functional groups.
Article
Chemistry, Organic
Gauthier Lefebvre, Olivier Charron, Janine Cossy, Christophe Meyer
Summary: Radical addition of SF5Cl to cyclopropenes was investigated to access SF5-cyclopropyl building blocks. The reaction shows regioselectivity at the less substituted carbon and moderate to high levels of diastereocontrol in chlorine atom transfer. The resulting adducts can undergo subsequent radical reduction or radical cyclization.
Article
Chemistry, Organic
Xiaoling Liu, Haimei Liu, Chang Bian, Ke-Hu Wang, Junjiao Wang, Danfeng Huang, Yingpeng Su, Xiaobo Lv, Yulai Hu
Summary: A new and efficient method for the synthesis of polysubstituted 3-trifluoromethyl-1,2,4-triazolines and their derivatives is described, involving a tandem addition/cyclization reaction between trifluoromethylN-acylhydrazones and cyanamide. The method offers mild reaction conditions, a broad substrate scope, good product yields, and atom economy.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Heng-Tong Qu, Zeng-Hui Wu, Guo-Chen Zhong, Yan-Chun Zhang, Cheng-Tao Feng, Kun Xu
Summary: An aerobic Mn(III)-catalyzed one-pot three-component synthesis of 5-cyano-pyrazolo[1,5-a]pyrimidines has been developed, which relies on the synergistic combination of Strecker reaction and oxidatively-induced 6 pi-azacyclization. This protocol offers a step-economic, regioselective, and functionally tolerant strategy to obtain 5-cyano-pyrazolo[1,5-a]pyrimidines, distinct from previous reports using toxic cyanating agents or multistep synthesis.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Sandeep Kumar, Daksh Singh Davas, Krishnendu Bar, Dinesh Kumar Gopalakrishnan, Deepesh Kumar, Tarak Karmakar, Janakiram Vaitla
Summary: In this paper, the synthesis of pi-conjugation-extended vinyl sulfoxonium ylides from vinyl sulfoxonium ylide and electron-deficient alkynes is reported. The new dienoate ylides are utilized in various transformations, including X-H (X = S, O) insertion, halogenation, carbene-mediated transformation, and radical-mediated reductions, to obtain a range of conjugated dienoates.
Article
Chemistry, Organic
Dan Luo, Liangzhen Hu, Tianyong Gao, Xiaohui Zhang, Yan Xiong
Summary: In this study, a series of polycyclic compounds with altenuene backbone were successfully synthesized through PhI(OAc)2-oxidized dearomatization and diesterification. The Umpolung diesterification reaction occurred under mild conditions without the need for an additional nucleophilic reagent. This provides a concise method for the synthesis of diverse natural altenuene analogues.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Youhao Wei, Zheng Wang, Kaifeng Wang, Jiang-Kai Qiu, Zhaoshan Wang, Haotian Li, Xiu Duan, Kai Guo, Xiaoguang Bao, Xinxin Wu
Summary: This study reports a copper-catalyzed allenic C(sp(2))-H cyanation with exceptional site-selectivity, addressing the challenge in synthetic chemistry of functionalizing allenic C(sp(2))-H bonds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Rui Li, Kai Wei, Wen Chen, Liang Li, Hongbin Zhang
Summary: A new process for the construction of 3,4,5-substituted isothiazoles is reported in this paper, utilizing reaction cascades including Pummerer-like rearrangement, nucleophilic condensation, and sulfenamide cyclization under mild conditions. This process provides good to excellent yields of isothiazoles bearing fluorine and other functional groups from readily available starting materials.
Article
Chemistry, Organic
Li Jing, Zhong-Jun Li, Er-Qing Li
Summary: We have developed a new 1,3-bis-electrophilic motif and applied it in palladium-catalyzed (3 + 2) annulations. This method offers a straightforward approach to constructing functionalized pyrrolidines with good yields. Importantly, the configuration (Z/E) of the 1,3-bis-electrophilic motif does not affect the yield and chemoselectivity of the reaction. Furthermore, preliminary asymmetric investigations using Pd(0)/thiourea synergistic catalysis resulted in moderate enantioselectivity.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Yolanda Navarro, Jesus Garcia Lopez, Maria Jose Iglesias, Fernando Lopez Ortiz
Summary: Through a ligand-free domino copper(I)-catalyzed azide-alkyne-azide process, 1,4-(disubstituted)-5-triazenyl-1,2,3-triazoles were synthesized successfully, and the crucial role of Cu-chelation in the interception of the intermediate by the azide was revealed through DFT calculations and X-ray diffraction analysis.
Article
Chemistry, Organic
S. Roe, M. Gunaratnam, C. Spiteri, P. Sharma, R. D. Alharthy, S. Neidle, J. E. Moses
ORGANIC & BIOMOLECULAR CHEMISTRY
(2015)
Article
Pharmacology & Pharmacy
Paul A. Stanley, Christian Spiteri, Jonathan C. Moore, Andrew S. Barrow, Pallavi Sharma, John E. Moses
CURRENT PHARMACEUTICAL DESIGN
(2016)
Article
Chemistry, Organic
Li-Chen Han, Paul A. Stanley, Paul J. Wood, Pallavi Sharma, Anchala I. Kuruppu, Tracey D. Bradshaw, John E. Moses
ORGANIC & BIOMOLECULAR CHEMISTRY
(2016)
Article
Chemistry, Organic
Shreesha V. Bhat, David Robinson, John E. Moses, Pallavi Sharma
Article
Chemistry, Organic
Pallavi Sharma, Shreesha Bhat, M. R. Ranga Prabhath, Andrew Molino, Elisa Nauha, David J. D. Wilson, John E. Moses
Article
Chemistry, Organic
Kimberley J. Powell, Joanna L. Richens, Jonathan P. Bramble, Li-Chen Han, Pallavi Sharma, Paul O'Shea, John E. Moses
Article
Chemistry, Multidisciplinary
Luke A. Adams, Pooja Sharma, Biswaranjan Mohanty, Olga V. Ilyichova, Mark D. Mulcair, Martin L. Williams, Ellen C. Gleeson, Makrina Totsika, Bradley C. Doak, Sofia Caria, Kieran Rimmer, James Horne, Stephen R. Shouldice, Mansha Vazirani, Stephen J. Headey, Brent R. Plumb, Jennifer L. Martin, Begona Heras, Jamie S. Simpson, Martin J. Scanlon
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2015)
Article
Chemistry, Multidisciplinary
Jonathan C. Moore, E. Stephen Davies, Darren A. Walsh, Pallavi Sharma, John E. Moses
CHEMICAL COMMUNICATIONS
(2014)
Article
Chemistry, Organic
Kimberley J. Powell, Li-Chen Han, Pallavi Sharma, John E. Moses
Article
Chemistry, Organic
Pallavi Sharma, M. R. Ranga Prabhath, Derek Wong, Maame Adjoa Ampem-Lassen, Shreesha Bhat, Luke Williams, Teresa G. Carvalho
Summary: In this study, a novel spiroannulation reaction of exoimines with 1,3-dipoles was demonstrated for the first time, leading to the synthesis of 3D spirocycles with a secondary amine in the spiro-ring. This synthetic method provides access to previously unexplored heterospirocyclic cores, with potential applications in the discovery of functional molecules for medicinal and materials science. The discovery of a new class of heterospirocycles with antimalarial activity against P. falciparum further confirms the potential of this approach.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Christopher J. Smedley, Andrew S. Barrow, Christian Spiteri, Marie-Claire Giel, Pallavi Sharma, John E. Moses
CHEMISTRY-A EUROPEAN JOURNAL
(2017)
