Article
Chemistry, Multidisciplinary
Kanji Niwa, Masao Ohashi, Kaili Xie, Chen-Yu Chiang, Cooper S. Jamieson, Michio Sato, Kenji Watanabe, Fang Liu, K. N. Houk, Yi Tang
Summary: We have discovered biosynthetic pathways that can produce and transform conjugated octaenes and nonaenes into complex natural products. The biosynthesis of (-)-PF1018 involves an enzyme called PfB, which controls the regio-, stereo-, and periselectivity of multiple reactions starting from a conjugated octaene. By using PfB as a starting point, we found a homologous enzyme, BruB, that facilitates diene isomerization, tandem 8π-6π-electrocyclization, and a 1,2-divinylcyclobutane Cope rearrangement to generate a novel compound not previously found in nature.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Lincong Sun, Haohua Chen, Bingxian Liu, Junbiao Chang, Lingheng Kong, Fen Wang, Yu Lan, Xingwei Li
Summary: This study reports the rhodium(III)-catalyzed C-H activation of anilines bearing an N-isoquinolyl directing group for oxidative [3+2] annulation with four classes of internal alkynes, leading to atroposelective indole synthesis via dynamic kinetic annulation with C-N reductive elimination constituting the stereo-determining step. The reaction proceeds under mild conditions with high regio- and enantioselectivity and functional group compatibility.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Acoustics
Ingrid V. Machado, Jhonathan R. N. dos Santos, Marcelo A. P. Januario, Arlene G. Correa
Summary: By utilizing ultrasound-assisted multicomponent reactions under heterogeneous catalysis, it is possible to efficiently synthesize biologically active organic compounds with reduced costs and energy consumption.
ULTRASONICS SONOCHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Pratyush Kumar Mishra, Nirmali Sharma, Hyunwoo Kim, Changwook Lee, Hyun-Woo Rhee
Summary: GEN-Click is a genetically encoded copper-click reaction that allows spatial biotin labeling of azide or alkyne-tagged biomolecules in live cells. It provides a genetically controlled, spatially restricted, metal-catalyzed biorthogonal reaction for labeling various azido-bearing biomolecules.
ACS CENTRAL SCIENCE
(2023)
Article
Chemistry, Organic
Mykyta Ziabko, Blanka Klepetarova, Petr Beier
Summary: A new stable fluorinated azide called azidodifluoromethylphenyl sulfone was synthesized from difluoromethyl phenyl sulfone on a multi-gram scale. This azide showed synthetic utility in the preparation of N-difluoro-(phenylsulfonyl)-methyl-1,2,3-triazoles through azide-alkyne cycloaddition reactions. It also served as a synthetic equivalent of the azidodifluoromethylanion.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Dat P. Nguyen, Huong T. H. Nguyen, Loi H. Do
Summary: Research on intracellular catalysis requires an interdisciplinary approach and state-of-the-art instruments. The lack of quantitative data has somewhat hindered progress in catalyst development, but recent advances in characterization methods may help overcome these limitations. Intracellular catalysis has great potential for future biotechnologies and therapeutics.
Article
Chemistry, Organic
Dongsheng Xue, Yonglei Que, Hao Shao, Haibing He, Xiaoli Zhao, Shuanhu Gao
Summary: The study on excited-state Nazarov reactions of dicyclicvinyl ketones showed their potential in synthesizing complex natural products, by constructing core tricyclic compounds with specific stereochemistry.
Article
Chemistry, Multidisciplinary
Shuaizhong Zhang, Jinquan Zhang, Hongbin Zou
Summary: Rh-catalyzed selective C-H functionalization of indoles was achieved using two different routes: alkenylation-annulation with the addition of KHSO4 and alkenylation-elimination in the presence of CsOAc. Notably, one-pot hydrolysis and benzoylation of the annulation products yielded easily separable beta-(1H-indol-2-yl)-beta-amino acid derivatives.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Elena Shaitanova, Vaclav Matousek, Tadeas Herentin, Martin Adamec, Robert Matyas, Blanka Klepetarova, Petr Beier
Summary: This article introduces a new method for preparing fluorinated azidoethane and its application in various reactions.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Mahesh K. Lakshman, Dellamol Sebastian, Padmanava Pradhan, Michelle C. Neary, Alexis M. Piette, Samuel P. Trzebiatowski, Alexander E. K. Henriques, Patrick H. Willoughby
Summary: A modular platform for facile access to H4-carbazolones and H2-indolones is described. The synthesis of the required compounds and their further transformation are achieved through different reaction steps.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Minghe Sun, Min Liu, Changkun Li
Summary: The chemodivergent regio- and enantioselective allylic alkylation of indoles catalyzed by Rh/bisoxazolinephosphane enables the selective formation of chiral C3- and N1-allylindoles with high branched/linear ratio and up to 99% ee by adjusting the counteranion of Rh, the allylic carbonate, reaction temperature, and the ligand.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Review
Crystallography
Weiqing She, Zhenzhen Xu, Lianjie Zhai, Junlin Zhang, Jie Huang, Weiqiang Pang, Bozhou Wang
Summary: Due to the introduction of oxygen atoms, N-oxide energetic compounds possess unique advantages in terms of oxygen balance, detonation properties, and energy density, which have attracted extensive attention from researchers worldwide. This article provides a comprehensive review of the synthetic strategies for two categories of N-oxides, azine N-oxides and azole N-oxides, and discusses the reaction mechanisms of aromatic N-oxide frameworks and their applications in creating high-energy substances. Furthermore, the energetic properties of N-oxide energetic compounds are compared and summarized.
Article
Chemistry, Multidisciplinary
Cheng-Zhou Lin, Ling-Feng Jiang, Guang-Yi Zhang, Fang-Shuai Zhou, Shao-Hua Wu, Jing Cao, Qing-Hai Deng
Summary: A copper-catalyzed asymmetric dearomative azidation of tryptamines using azidobenziodoxolone as a reagent is developed, giving access to a range of 3a-azido-pyrroloindolines in high enantioselectivities under mild conditions. The resulting azides can be readily transformed into the corresponding 3a-amino-pyrroloindolines via reduction or 1,2,3-triazole derivatives via a click reaction.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Applied
Teppei Abe, Kazuki Kobayashi, Seiya Kikukawa, Yuuki Kanai, Takeshi Hata
Summary: This study investigated the reaction of 1-azido-2-(2,2-dihalovinyl)arenes with Rh2(esp)2 catalyst, successfully synthesizing 2,3-dihaloindoles and 2-haloquinoxaline. In the reaction of the 2-chloro-2-iodovinyl group, the iodo group selectively rearranged to yield 2-chloro-3-iodoindoles.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Applied
Cheng Li, Bin Zhao, Guojiang Mao, Guo-Jun Deng
Summary: We developed a redox-neutral synthesis of indenones catalyzed by rhodium(III), which does not require harsh conditions or any external oxidants. Mechanistic experiments and DFT calculation revealed that the reaction involves various cascade processes.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
