Organic chemistry articles within Nature Communications

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  • Article
    | Open Access

    Pentavalent stereocentres encode an expanded stereochemical space, but their catalytic tractability remained unprecedented. In this report, the authors report that catalyst control over pentavalent stereocentres is feasible.

    • Anton Budeev
    • , Jianyang Dong
    •  & Christof Sparr

  • Article
    | Open Access

    Visible light-induced glycosylation reactions are achieved by either photoactivating a photosensitizer or using a stoichiometric activator, while glycosylation via a photoactive glycosyl donor was so far not reported. In this study, the authors develop a photosensitizer free visible-light-mediated glycosylation approach using photoactive 2-glycosyloxy tropone as the donor, obtaining a wide range of O-glycosides or oligosaccharides.

    • Jing Zhang
    • , Zhao-Xiang Luo
    •  & De-Cai Xiong

  • Article
    | Open Access

    The combination of electrochemistry and photochemistry in the context of organic synthesis is in its infancy. Here, the authors report selective C(sp3)–H arylation/alkylation of alkanes, using Earth-abundant bimetallic transition metal catalysis, under photo- and electrochemical conditions.

    • Long Zou
    • , Siqi Xiang
    •  & Qingquan Lu

  • Article
    | Open Access

    Fused carbocycles are key structural elements of molecules in nature and they are often found in drugs and organic materials, but bicyclic systems containing six and seven-membered rings are difficult to prepare. Here, the authors functionalize an azulene skeleton that consists of fused five and seven-membered rings and carry out a ring expansion reaction to afford the desired bicycles.

    • Sangjune Park
    • , Cheol-Eui Kim
    •  & Phil Ho Lee

  • Article
    | Open Access

    Dicarbofunctionalization of nonactivated alkenes is a simple way to rapidly build molecular complexity, but these transformations have not been extensively explore under metallaphotoredox conditions. Here, the authors develop a nickel/photoredox dual catalytic system for arylalkylation of alkenes.

    • Yuxi Gao
    • , Lijuan Gao
    •  & Chengfeng Xia

  • Article
    | Open Access

    Multicomponent cross-coupling of alkenes with silicon reagents is used to yield complex silicon-containing compounds from readily accessible feedstock chemicals but the reaction with simple alkenes remains challenging. Here, the authors report a regioselective silylalkylation of simple alkenes, which is enabled by using a stable Ni(II) salt and an inexpensive trans-1,2-diaminocyclohexane ligand as a catalyst.

    • Chao Ding
    • , Yaoyu Ren
    •  & Guoyin Yin

  • Article
    | Open Access

    Despite the rich coordination chemistry, hydroxylamines are rarely used as ligands for transition metal coordination compounds. Here the authors designed macrocyclic poly-N-hydroxylamines that form complexes containing a d-metal ion and coordinate by up to six hydroxylamine fragments.

    • Vladislav K. Lesnikov
    • , Ivan S. Golovanov
    •  & Alexey Yu. Sukhorukov

  • Article
    | Open Access

    While carbon-introducing difunctionalization of C-C double bonds is well established, the analogous difunctionalization for introducing germanium group and other functionalities remains elusive. Here, the authors describe a nickel-catalyzed germylative alkylation of activated olefins with easily accessible primary, secondary and tertiary alkyl bromides and chlorogermanes as the electrophiles to form C-Ge and C-Calkyl bonds simultaneously.

    • Rui Gu
    • , Xiujuan Feng
    •  & Xuan Zhang

  • Article
    | Open Access

    Recently, the asymmetric bifunctionalization of alkenes has received much attention but the development of enantioselective alkoxyalkenylation has posed a considerable challenge and has lagged largely behind. Here, the authors report a palladium-catalyzed enantioselective alkoxyalkenylation reaction, using a range of primary, secondary, and tertiary γ-hydroxyalkenes with alkenyl halides.

    • Shuai Zhu
    • , Zihao Ye
    •  & Junliang Zhang

  • Article
    | Open Access

    Low-valent nickel(0) complexes that promote α-functionalization of carbonyls leveraging its pro-nucleophilic character in conjunction with olefin acceptors are very scarce despite their attractivity. Here, the authors report a Ni(0)NHC catalyst which converts ketones and non-conjugated dienes to synthetically highly valuable α-allylated products.

    • Yi-Xuan Cao
    • , Matthew D. Wodrich
    •  & Nicolai Cramer

  • Article
    | Open Access

    The chiral allene formation reactions catalyzed by palladium occur via a syn elimination mechanism, but there is a lack in understanding of the stereoselectivity in rhodium catalyzed reactions, specifically the β-OH elimination step. Here, the authors report the sterically controlled Rh-catalyzed SN2’-type substitution reactions of tertiary propargylic alcohols with arylmetallic species affording the non-readily available enantioenriched tetrasubstituted allenes via either exclusive syn- or anti-β-OH elimination.

    • Jie Wang
    • , Wei-Feng Zheng
    •  & Shengming Ma

  • Article
    | Open Access

    The use of heteroatom-centered anions as super-electron-donors (SEDs) for direct single-electron-transfer reactions has rarely been studied. Here, the authors show that heteroatom anions can be applied as SEDs to initiate radical reactions for synthesis of 3-substituted benzofurans, which have applications in both organic synthesis and pesticide development.

    • Shichun Jiang
    • , Wei Wang
    •  & Yonggui Robin Chi

  • Article
    | Open Access

    Saturated N-heterocyclic pyrrolidines are common in natural products and medicinal compounds, but reconstruction of their skeletal structures to access new chemical space is a challenging. Here, the authors report a skeletal modification strategy for conversion of polar cyclic pyrrolidines into nonpolar linear dienes through a N-atom removal and deconstruction process.

    • Haitao Qin
    • , Ting Guo
    •  & Hongjian Lu

  • Article
    | Open Access

    Developing eco-friendly chiral organocatalysts with the combined advantages of homogeneous catalysis and heterogeneous processes is challenging. Here, the authors present, a family of amphiphilic one handed helical polyisocyanides bearing phosphine pendants which self-assembled into well-defined chiral micelles in water and show thermo-responsiveness

    • Lei Xu
    • , Li Zhou
    •  & Zong-Quan Wu

  • Article
    | Open Access

    Traditional metallaphotocatalysis often requires two or more separate catalysts and is considered to be costly and not tolerant towards a wide substrate scope. Here the authors realize metallaphotocatalysis with a bifunctional dirhodium tetracarboxylate as single catalyst component to merge carbenoid chemistry and 1O2 chemistry.

    • Taoda Shi
    • , Tianyuan Zhang
    •  & Wenhao Hu

  • Article
    | Open Access

    The development of chemically diverse boron-oxygen-fused polycyclic aromatic hydrocarbons has been limited by their synthetic complexity. Here, authors report a one-pot strategy for their facile synthesis and demonstrate their potential as ultralong afterglow and host materials for deep-blue OLEDs.

    • Guijie Li
    • , Kewei Xu
    •  & Yuan-Bin She

  • Article
    | Open Access

    The formal C–C bond insertion into aldehydes is an attractive methodology for the assembly of homologated carbonyl compounds but the homologation of aldehydes has been limited to diazo approach and the enantioselective reaction was rarely developed. Here, the authors report an asymmetric formal C–C bond insertion into aldehydes through diyne cyclization strategy

    • Cui-Ting Li
    • , Lin-Jun Qi
    •  & Bo Zhou

  • Article
    | Open Access

    Alkylphosphonates are used as chargeneutral replacements for naturally-occurring phosphodiester backbones in nucleotides but the choice of alkyl moieties that can be attached to phosphorus atoms in these compounds is limited to methyl groups or primary/secondary alkyls. Here, the authors demonstrate the tertiary alkylation of the phosphorus atoms of phosphites bearing two 2’-deoxynuclosides using a carbocation generated via a light-driven radical-polar crossover mechanism

    • Kenji Ota
    • , Kazunori Nagao
    •  & Hirohisa Ohmiya

  • Article
    | Open Access

    The development of carbonylative reactions with CO gas under mild conditions are important in organic synthesis. Here, the authors demonstrate an earth-abundant nickel-catalyzed three-component tandem acylzincation/cyclization sequence of allene and alkylzinc reagent with 1 atm of CO.’

    • Xianqing Wu
    • , Chenglong Wang
    •  & Yifeng Chen

  • Article
    | Open Access

    Although aryl triflates are essential building blocks in organic synthesis, the applications as aryl radical precursors are limited. Here, the authors report an organomediated electrochemical strategy for the generation of aryl radicals from aryl triflates, providing a method for the synthesis of aryl sulfonyl fluorides from feedstock phenol derivatives under very mild conditions.

    • Xianqiang Kong
    • , Yiyi Chen
    •  & Zhong-Yan Cao

  • Article
    | Open Access

    Remote meta selective C–H Functionalization of aromatic compounds remains challenging in chemical synthesis. Here, the authors report an iridium catalyst bearing a bidentate pyridine-pyridone ligand framework that efficiently catalyzes this meta selective borylation reaction.

    • Saikat Guria
    • , Mirja Md Mahamudul Hassan
    •  & Buddhadeb Chattopadhyay

  • Article
    | Open Access

    Alkyl halides, widely recognized as important building blocks and reagents in organic synthesisbut generating alkyl radicals directly from unactivated alkyl halides under mild conditions remains a challenge. Here the authors report an effective electrooxidation strategy for generating alkyl radicals from unactivated alkyl iodides via an electrochemical halogen-atom transfer process under mild conditions

    • Xiang Sun
    •  & Ke Zheng

  • Article
    | Open Access

    In nature, α-helical peptides adopt right-handed conformations dictated by L-amino acids, but isolating one-handed α-helical peptides composed of only achiral components remains a challenge. Here, the authors achieve this by optical resolution of the corresponding racemic (quasi-)static α-helical peptide with double stapling, which effectively freezes the interconversion between the right-handed (P)- and left-handed (M)-α-helices.

    • Naoki Ousaka
    • , Mark J. MacLachlan
    •  & Shigehisa Akine

  • Article
    | Open Access

    Quaternary amino acids are important building blocks and precursors of medicinal compounds. Here, the authors describe a copper-catalyzed regiodivergent electrochemical core structure-oriented crossdehydrogenative coupling reaction of Schiff bases and commercially available hydroquinones to obtain three classes of chiral quaternary amino acid derivatives

    • Tian Xie
    • , Jianming Huang
    •  & Chang Guo

  • Article
    | Open Access

    The reaction mechanism of the historic copper-catalyzed Glaser coupling has been debated to be based on redox cycles of Cu ions in specific oxidation states or on a radical mechanism based on Cu(0)/Cu(I). Here, the authors demonstrate two coexisting Glaser coupling pathways which can be differentiated by anaerobic/irradiation or aerobic reaction conditions

    • Siqi Zhang
    •  & Liang Zhao

  • Article
    | Open Access

    Photocatalytic selective C(sp3)–H activation/cross-coupling reactions are appealing in organic synthesis. Here the authors describe the development of excited-state Pd-catalyzed dehydrogenative β-sulfonylation reactions using amines and aryl sulfonyl chlorides via intermolecular hydrogen atom transfer and C−S cross-coupling processes at room temperature.

    • Krishnamoorthy Muralirajan
    • , Rajesh Kancherla
    •  & Magnus Rueping

  • Article
    | Open Access

    Organoboron compounds are of high interest in organic synthesis due to the versatility of boryl substituents that allows access to further modifications. Here, the authors report on the development of an oxidative C(sp3)−H borylation reaction under metal- and oxidant-free conditions, enabled by photoelectrochemical strategy

    • Ping-Fu Zhong
    • , Jia-Lin Tu
    •  & Wujiong Xia

  • Article
    | Open Access

    Methods to construct 1,2-diols have previously been developed, but often require the participation of a metal and are limited to activated alkenes. Here, the authors report a metal-free electrochemical dihydroxylation of unactivated alkenes providing valuable and versatile dihydroxylated products.

    • Min Liu
    • , Tian Feng
    •  & Youai Qiu

  • Article
    | Open Access

    The activation of ethers by weak interactions in supramolecular catalysis remains challenging. Here, the authors describe an activation mode based on dual Se···π and Se···O bonding, that can activate benzylic as well as allylic ether C-O σ-bonds to achieve cyclization, coupling and elimination reactions.

    • Zhiguo Zhao
    • , Yuanling Pang
    •  & Yao Wang

  • Article
    | Open Access

    Sp2 carbon nucleophiles are generally not considered for transition metal-catalyzed asymmetric hydrofunctionalizations of unsaturated bonds due to challenges in cleaving corresponding inert sp2 C-H bonds. Here, the authors report a protocol to achieve asymmetric formal sp2 hydrocarbonations, including hydroalkenylation, hydroallenylation and hydroketenimination of both 1,3-dienes and alkynes via hydroalkylation and Wittig reaction cascade

    • Ming-Qiao Tang
    • , Zi-Jiang Yang
    •  & Zhi-Tao He

  • Article
    | Open Access

    The phenyl ring is a basic structural element in chemistry. Here, the authors show the design, synthesis, and validation of 2-oxabicyclo[2.2.2]octane as a new saturated bioisostere with improved physicochemical properties

    • Vadym V. Levterov
    • , Yaroslav Panasiuk
    •  & Pavel K. Mykhailiuk

  • Article
    | Open Access

    Carbon nanosolenoid materials with Riemann surfaces have unique structures and novel physical properties. Here, the authors report a nitrogen-doped carbon nanosolenoid heterojunction material with distinctive photocatalytic properties for light driven hydrogen production and organic transformations.

    • Yu Zhou
    • , Xinyu Zhang
    •  & Pingwu Du

  • Article
    | Open Access

    The nucleophilic substitution reaction (SN2) is one of the oldest yet very useful organic transformations, but surprisingly, the nucleophilic character of isocyanides has never been explored in SN2 reactions. Here the authors show that isocyanides react as versatile nucleophiles in SN2 reactions with alkyl halides in a general manner to afford highly substituted secondary amides by in situ hydrolysis of the intermediate nitrilium ion.

    • Pravin Patil
    • , Qiang Zheng
    •  & Alexander Dömling

  • Article
    | Open Access

    Catalytic asymmetric a-alkylation of carbonyl compounds represents a longstanding challenge in synthetic organic chemistry but general methods for the catalytic symmetric alkylation of carbonyl compounds remain elusive. Here, the authors mine and engineer methyltransferases as synthetically useful biocatalysts for the catalytic asymmetric alkylation reactions of carbonyl compounds.

    • Shuyun Ju
    • , Kaylee P. Kuzelka
    •  & Yang Yang

  • Article
    | Open Access

    Azulene-based conjugated systems are of great interests due to their unusual structures and photophysical properties but incorporation of a transition metal into azulene skeleton presents remains elusive. Here, the authors describe an efficient [5 + 2] annulation reaction for the rapid construction of a metalla-dual-azulene.

    • Hai-Cheng Liu
    • , Kaidong Ruan
    •  & Haiping Xia

  • Article
    | Open Access

    Silicon-stereogenic optically active silylboranes could potentially allow the formation of chiral silyl nucleophiles as well as the synthesis of various chiral silicon compounds but the synthesis of such silicon-stereogenic silylboranes remains underdeveloped. Here, the authors report the synthesis of silicon-stereogenic optically active silylboranes via a stereospecific Si–H borylation of chiral hydrosilanes in high yield enantiospecificity

    • Xihong Wang
    • , Chi Feng
    •  & Hajime Ito

  • Article
    | Open Access

    The Mannich reaction is a well-established method for the synthesis of β-amino carbonyl compounds while the analogous reactions of homo-enol or its equivalents with imines or iminium ions are much less explored. Here, the authors describe a homo-Mannich reaction of cyclopropanol with imines generated via a Bischler-Napieralski reaction.

    • Hanyue Qiu
    • , Xinghai Fei
    •  & Min Zhang

  • Article
    | Open Access

    While a variety of well-established methods enable the control of a stereogenic center, a catalytic method for controlling a stereogenic axis in one substrate is typically unavailable for controlling axial chirality in other substrates with a similar structure. Here, the authors report o-amidobiaryl as a flexible platform for chiral phosphoric acid catalyzed atroposelective dynamic kinetic resolution.

    • Ahreum Kim
    • , Chanhee Lee
    •  & Yongseok Kwon

  • Article
    | Open Access

    Atropisomers are an important chiral system which are widely present in natural products but atropisomerism bearing a N−N bond remains largely underdeveloped. Here, the authors report an efficient method for the enantioselective synthesis of N−N axially chiral frameworks under mild conditions via a cobalt-catalyzed atroposelective C-H activation/annulation

    • Tong Li
    • , Linlin Shi
    •  & Jun-Long Niu

  • Article
    | Open Access

    Classical metalation reactions in organic synthesis typically involve metal-halogen exchange. Here, the authors introduce a metal-carbon exchange strategy that enables the skeletal editing of biologically relevant lactams by a Ni(0) compound.

    • Hongyu Zhong
    • , Dominic T. Egger
    •  & Bill Morandi

  • Article
    | Open Access

    The catalytic asymmetric dearomatization (CADA) reaction is a powerful protocol for the assembly of three-dimensional cyclic compounds but phenols have been considered challenging substrates. Here, the authors report the chiral phosphoric acidcatalyzed divergent intermolecular CADA reactions of phenols with azoalkenes to obtain tetrahydroindolone and cyclohexadienone products in good yields with excellent ee values.

    • Xiang Gao
    • , Tian-Jiao Han
    •  & Guang-Jian Mei

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