Diversity-oriented synthesis articles within Nature Communications

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  • Article
    | Open Access

    The direct C−H-difluoromethylation of pyridines represents a highly efficient economic way to access azines. However, the direct meta-difluoromethylation of pyridines remains elusive. Here, the authors demonstrate switchable meta- as well as para-C−H difluoromethylation of pyridines through radical processes by using oxazino pyridine intermediates.

    • Pengwei Xu
    • , Zhe Wang
    •  & Armido Studer

  • Article
    | Open Access

    Directing group strategies have been used extensively in C–H activation reactions but current methods rely heavily on coordination with nitrogen or oxygen atoms in molecules and have therefore been found to exhibit limited generality in asymmetric syntheses. Here, the authors report enantioselective C–H activation with unsaturated hydrocarbons directed by phosphorus centres to rapidly construct libraries of axially chiral phosphines through dynamic kinetic resolution.

    • Zexian Li
    • , Minyan Wang
    •  & Zhuangzhi Shi

  • 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

    The dearomative functionalization of aromatic compounds represents a challenging transformation, as it typically needs to overcome a great kinetic barrier. Here, the authors disclose a weak-bond-accelerated, catalyst-free dearomative [3,3]-rearrangement of o-nitrophenyl alkyne for the divergent synthesis of benzazepines and bridged polycycloalkanones via remote oxygen transposition.

    • Qiu Shi
    • , Zhehui Liao
    •  & Shifa Zhu

  • Article
    | Open Access

    The Mannich reaction is a three-component reaction for preparing alkylamines, but the nucleophilic components rely on C(sp2)−H and activated C(sp3)−H bonds. Here, the authors report an unprecedented multicomponent double Mannich alkylamination for both C(sp2)−H and unactivated benzylic C(sp3)−H bonds.

    • Zhencheng Lai
    • , Rongkai Wu
    •  & Sunliang Cui

  • Article
    | Open Access

    The generation of non-stabilized alkyl radicals from sulfonium salts has been a challenge for several decades. Here, the authors show the treatment of S-(alkyl) thianthrenium salts, which can generate non-stabilized alkyl radicals as key intermediates that enable controlled and selective reactions under mild photoredox conditions.

    • Cheng Chen
    • , Zheng-Jun Wang
    •  & Zhuangzhi Shi

  • Article
    | Open Access

    O-GalNAc glycans are essential in many biological and pathological processes, but difficult to access due to their structural complexity and synthetic challenges. Here, the authors report an efficient chemoenzymatic modular assembly strategy to construct structurally diverse O-GalNAc glycans, use the synthesised glycans to generate a synthetic mucin O-glycan microarray and profile binding specificities of glycan-binding proteins.

    • Shuaishuai Wang
    • , Congcong Chen
    •  & Lei Li

  • Article
    | Open Access

    Nanographenes are emerging as a distinctive class of functional materials for electronic and optical devices. Here, the authors develop a facile strategy to recompose helicenes into a variety of chiral nanographenes through an oxidative cyclo-rearrangement reaction.

    • Chengshuo Shen
    • , Guoli Zhang
    •  & Huibin Qiu

  • Article
    | Open Access

    Metal-free olefin diamination may display challenges, especially when targeting fluorinated amines. Here, the authors report a double nucleophilic functionalization of an activated alkene originated from a trifluoropropenyliodonium salt with two nucleophiles for the selective synthesis of trifluoromethylated ethylene amines and diamines.

    • Ferenc Béke
    • , Ádám Mészáros
    •  & Zoltán Novák

  • Article
    | Open Access

    Combining the Heck reaction with other transformations provides a powerful strategy to access diverse, complex compounds. Here, the authors report a weak coordination dominated Pd(0)-catalyzed quadruple C-H activation followed by hydro-functionalization, C-H silylation, and C-H borylation.

    • Bo-Cheng Tang
    • , Wen-Xuan Lin
    •  & An-Xin Wu

  • Article
    | Open Access

    Skeletal reorganizations are intriguing processes in chemical synthesis due to their mechanism, atom-economy and synthetic versatility. Herein, the authors describe a divergent skeletal reorganization of N-sulfonyl ynamides to thiete sulfones and propargyl sulfonamides.

    • Linwei Zeng
    • , Yuxin Lin
    •  & Sunliang Cui

  • Article
    | Open Access

    Alkyl carboxylic acids and primary amines are ubiquitous and useful for synthesis of new compounds. Here, the authors report a manganese-mediated reductive decarboxylative/deaminative functionalization of activated aliphatic acids and primary amines for construction of C-C and C-X bonds under mild conditions.

    • Zhan Li
    • , Ke-Feng Wang
    •  & Honggen Wang

  • Article
    | Open Access

    The direct cleavage of C(CO)−C single bonds is usually restricted to strained ketone substrates or to chelating assistance. Here, the authors show a rhodium(II)-catalyzed three-component reaction of 1,3-diones, diazoesters, and DMF, leading to an unusual formal insertion of O–C(sp3)–C(sp2) into unstrained C(CO)–C bonds.

    • Dan Ba
    • , Si Wen
    •  & Guolin Cheng

  • Article
    | Open Access

    Selective C-H trifluoromethoxylation of pyridines remains a formidable synthetic challenge. Here, the authors report a silver-mediated late-stage C-H trifluoromethoxylation of arenes and heteroarenes as limiting reagents with trifluoromethoxide anion.

    • Zhijie Deng
    • , Mingxin Zhao
    •  & Pingping Tang

  • Article
    | Open Access

    Bryostatin 1 is a unique therapeutic lead, however its scarce natural sources have hampered its use in treatment of human disease. Here, the authors use a scalable synthesis of bryostatin 1 to make close-in analogs which potently induce increased cell surface expression holding potential for immunotherapy.

    • Clayton Hardman
    • , Stephen Ho
    •  & Paul A. Wender

  • Article
    | Open Access

    Transition metal-catalysed C–H hydroxylation is one of the most notable synthetic advances to access alcohols and phenols. Here, the authors report a metal-free, mild C–H hydroxylation of (hetero)arenes via boron-mediated chelation.

    • Jiahang Lv
    • , Binlin Zhao
    •  & Zhuangzhi Shi

  • Article
    | Open Access

    Derivatization of natural products is a powerful approach to generate new molecules for biological screenings. Here, the authors employ C-H oxidation and ring expansion methods for the preparation of a library of medium-sized ring skeleta, which occupy a unique chemical space based on chemoinformatic analysis.

    • Changgui Zhao
    • , Zhengqing Ye
    •  & Weiping Tang

  • Article
    | Open Access

    Dialkyl biaryl phosphines find wide application in catalysis as ligands. Here, the authors report a rhodium-catalysed hydroarylation of alkenes and alkynes with tertiary phosphines through P(III)-chelation assisted C-H activation affording a library of functionalized phosphines which hold potential in catalytic applications.

    • Dingyi Wang
    • , Ben Dong
    •  & Zhuangzhi Shi

  • Article
    | Open Access

    Diversity-oriented synthesis is a valuable strategy to construct complex molecules of medicinal interest. Here, the authors show a folding cascade strategy to convert linear substrates into polycyclic compounds with multiple stereocentres by combining the reductive chemistry of SmI2 with 1,5-hydrogen atom transfer.

    • Mateusz P. Plesniak
    • , Monserrat H. Garduño-Castro
    •  & David J. Procter

  • Article
    | Open Access

    Development of comprehensive structure–activity relationships for coronatine has been a major goal in the agrochemical industry. Here, the authors report the gram-scale production and structure–activity relationship of parent coronafacic acid and ultimately rationalise the biological activity of analogues of this phytotoxin.

    • Mairi M. Littleson
    • , Christopher M. Baker
    •  & Allan J. B. Watson

  • Article
    | Open Access

    Late-stage diversification of natural products is an important starting point for drug discovery. Here, the authors use chiral reagents to perform the regiocontrolled ring expansion of steroid precursors and achieve more than 100 isomerically pure analogs with spatial and functional diversity.

    • Manwika Charaschanya
    •  & Jeffrey Aubé

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