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ORGANIC CHEMISTRY FRONTIERS

21 MARCH 2021, ISSUE 6,
PAGE 1105 TO 1388


35 items

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CONTENTS LIST

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Research Article


SEQUENCE-CONTROLLED SUPRAMOLECULAR COPOLYMER CONSTRUCTED BY SELF-SORTING
ASSEMBLY OF MULTIPLE NONCOVALENT INTERACTIONS

Hui Li, Ying Yang, Fenfen Xu, Zhaozhao Duan, Riqiang Li, Herui Wen and Wei Tian

A sequence-controlled supramolecular copolymer was constructed by self-sorting
assembly of metal coordination and two types of host–guest interactions.


From the themed collection: FOCUS: Macrocyclic and supramolecular chemistry

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The article was first published on 28 Jan 2021
Org. Chem. Front., 2021,8, 1117-1124
https://doi.org/10.1039/D0QO01540G
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Research Article


REMOTE METHYLENE C(SP3)–H FUNCTIONALIZATION ENABLED BY ORGANOPHOSPHINE-CATALYZED
ALKYNE ISOMERIZATION

De Wang, Zefeng Song, Jianyu Zhang and Tao Xu

Non classical EWG-activated arylalkynes as C1 units in organophosphine catalyzed
diverse remote sp3 C–H functionalization.



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The article was first published on 09 Dec 2020
Org. Chem. Front., 2021,8, 1125-1131
https://doi.org/10.1039/D0QO01399D
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Research Article


HOLE-MEDIATED PHOTOREDOX CATALYSIS: TRIS(P-SUBSTITUTED)BIARYLAMINIUM RADICAL
CATIONS AS TUNABLE, PRECOMPLEXING AND POTENT PHOTOOXIDANTS

Shangze Wu, Jonas Žurauskas, Michał Domański, Patrick S. Hitzfeld, Valeria
Butera, Daniel J. Scott, Julia Rehbein, Ajeet Kumar, Erling Thyrhaug, Jürgen
Hauer and Joshua P. Barham

Triarylamines are demonstrated as novel, tunable electroactivated photocatalysts
that use dispersion precomplexation to harness the full potential of the visible
photon (>4.0 V vs. SCE) in anti-Kasha photo(electro)chemical super-oxidations of
arenes.


From the themed collection: Recent Open Access Articles in Frontiers Journals

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The article was first published on 03 Mar 2021
Org. Chem. Front., 2021,8, 1132-1142
https://doi.org/10.1039/D0QO01609H
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Research Article


SYNTHESIS OF POLYCYCLIC NAPHTHOLS AND NAPHTHALENES VIA TANDEM
TI(OI-PR)4-PROMOTED PHOTOENOLIZATION DIELS–ALDER REACTION AND AROMATIZATION

Xiao-Long Lu, Baochao Yang, Haibing He and Shuanhu Gao

An efficient approach to naphthol and naphthalene scaffolds has been developed
using a sequence involving tandem Ti(Oi-Pr)4-promoted photoenolization
Diels–Alder (PEDA) and aromatization reactions.



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The article was first published on 04 Jan 2021
Org. Chem. Front., 2021,8, 1143-1148
https://doi.org/10.1039/D0QO01346C
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Research Article


INTERMOLECULAR ALKENE ARYLCYANATION USING BNSCN AS A CYANIDE SOURCE VIA A
REDUCTIVE STRATEGY: ACCESS TO 3,3-DISUBSTITUTED OXINDOLES

Yunxia Feng, Shen Zhao, Guopeng Du, Shuang Zhang, Daopeng Zhang, Hui Liu, Xinjin
Li, Yunhui Dong and Feng-Gang Sun

Herein, a nickel-catalyzed two-component reductive arylcyanation of aryl
(pseudo)halide tethered alkenes using benzyl thiocyanate as a cyanide source via
C–S bond activation is developed.



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The article was first published on 06 Jan 2021
Org. Chem. Front., 2021,8, 1149-1154
https://doi.org/10.1039/D0QO01462A
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Research Article


REGIOSELECTIVE SYNTHESIS OF FUSED OXA-HETEROCYCLES VIA IODINE-MEDIATED
ANNULATION OF CYCLIC 1,3-DICARBONYL COMPOUNDS WITH PROPARGYLIC ALCOHOLS

Liang Zhang, Neng-Jie Mou, Dong-Rong Xiao, Xin Zhuang, Xiao-Long Lin, Tian Cai
and Qun-Li Luo

The synthesis of structurally diverse fused oxa-heterocycles is established
through the iodine-mediated cascade annulation of cyclic 1,3-dicarbonyl
compounds with propargylic alcohols.



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The article was first published on 11 Jan 2021
Org. Chem. Front., 2021,8, 1155-1162
https://doi.org/10.1039/D0QO01496F
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Research Article


CONSTRUCTING CHIRAL AZA-QUATERNARY CARBON CENTERS BY ENANTIOSELECTIVE
CARBONYLATIVE HECK REACTION OF O-IODOANILINES WITH ALLENES

Zhengshuai Xu, Chaoren Shen, Hongru Zhang, Peng Wang and Kaiwu Dong

The construction of chiral aza-quaternary C-centers via C–N bond formation is
achieved by a Pd-catalysed asymmetric carbonylative Heck reaction of
o-iodoanilines with allenes, providing chiral dihydroquinolinone derivatives
with moderate to high yield and enantiomeric ratio.



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The article was first published on 30 Dec 2020
Org. Chem. Front., 2021,8, 1163-1169
https://doi.org/10.1039/D0QO01486A
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Research Article


FUSED AMBIPOLAR AZA-ISOINDIGOS WITH NIR ABSORPTION

Liping Yao, Danlei Zhu, Hailiang Liao, Sheik Haseena, Mahesh Kumar Ravva,
Shengyu Cong, Liuyuan Lan, Yazhou Wang, Zhengke Li, Lang Jiang and Wan Yue

A series of large and extended novel electron-deficient aza-isoindigos with up
to 14 rings was synthesized exhibit excellent solubility, high EA, NIR
absorption,  planar backbonhole mobility of 0.076 cm2 V−1 s−1 and electron
mobility of 0.003 cm2 V−1 s−1.



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The article was first published on 08 Jan 2021
Org. Chem. Front., 2021,8, 1170-1176
https://doi.org/10.1039/D0QO01495H
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Research Article


ISOISHWARANE SYNTHASE FROM STREPTOMYCES LINCOLNENSIS

Houchao Xu, Jan Rinkel and Jeroen S. Dickschat

The product of a terpene synthase from Streptomyces lincolnensis has been
identified as the new natural product isoishwarane. The enzyme mechanism was
studied by isotopic labelling experiments and site-directed mutagenesis.



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The article was first published on 19 Jan 2021
Org. Chem. Front., 2021,8, 1177-1184
https://doi.org/10.1039/D0QO01583K
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Research Article


A NOVEL THREE-COMPONENT REACTION FOR CONSTRUCTING INDOLIZINE-CONTAINING
ALIPHATIC SULFONYL FLUORIDES

Hong-Ru Chen, Zhen-Yu Hu, Hua-Li Qin and Haolin Tang

A copper-catalyzed three-component reaction for transforming quinolines,
isoquinolines and pyridines to a class of indolizine-containing alkyl sulfonyl
fluorides was developed.



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The article was first published on 18 Jan 2021
Org. Chem. Front., 2021,8, 1185-1189
https://doi.org/10.1039/D0QO01430C
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Research Article


RHODIUM(III)-CATALYZED C–H ACTIVATION/ANNULATION OF N-IMINOPYRIDINIUM YLIDES
WITH ALKYNES AND DIAZO COMPOUNDS

Xiang Li, Ruihong Zhang, Yaoting Qi, Qing Zhao and Tuanli Yao

Rh(III)-Catalyzed C–H activation/annulation of N-iminopyridinium ylides with
alkynes and diazo compounds has been realized for the synthesis of isoquinolones
and isocoumarins.



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The article was first published on 18 Jan 2021
Org. Chem. Front., 2021,8, 1190-1196
https://doi.org/10.1039/D0QO01333A
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Research Article


GENERATION OF POWERFUL ORGANIC ELECTRON DONORS BY WATER-ASSISTED DECARBOXYLATION
OF BENZIMIDAZOLIUM CARBOXYLATES

Guillaume Tintori, Arona Fall, Nadhrata Assani, Yuxi Zhao, David Bergé-Lefranc,
Sébastien Redon, Patrice Vanelle and Julie Broggi

In situ and easy generation of organic electron donors from water-activation of
carboxylate precursors allows OED-promoted intermolecular radical addition
reactions.



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The article was first published on 22 Jan 2021
Org. Chem. Front., 2021,8, 1197-1205
https://doi.org/10.1039/D0QO01488E
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Research Article


DIAZADIBORININE AS AN AMBIPHILIC CATALYST FOR METAL-FREE HYDROGENATION: A
COMPUTATIONAL STUDY ON THE STRUCTURAL DESIGN AND REACTION MECHANISM

Youxiang Shao, Ming Huang, Fenglong Gu, Cunyuan Zhao, Ling-Bo Qu and Zhuofeng Ke

The reactivity and mechanism of hydrogenation by a metal-free ambiphilic
catalyst.



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The article was first published on 14 Jan 2021
Org. Chem. Front., 2021,8, 1206-1215
https://doi.org/10.1039/D0QO01510E
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Research Article


A PEGYLATED N-HETEROCYCLIC CARBENE-GOLD(I) COMPLEX: AN EFFICIENT CATALYST FOR
CYCLIZATION REACTION IN WATER

Bijin Lin, Xumu Zhang, Cong-Ying Zhou and Chi-Ming Che

A recyclable, PEGylated N-heterocyclic carbene(NHC)–gold(I) catalyst was
synthesized, which exhibited high reactivity and regio-selectivity in the
cyclization of alkynoic acids and cascade reaction of tryptamine and alkynoic
acids in water.



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The article was first published on 13 Jan 2021
Org. Chem. Front., 2021,8, 1216-1222
https://doi.org/10.1039/D0QO01266A
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Research Article


IRIDIUM-CATALYZED ASYMMETRIC HYDROGENATION OF N-PHOSPHINOYLIMINE

Congcong Yin, Yingmin Pan, Longsheng Zheng, Bijin Lin, Jialin Wen and Xumu Zhang

On catalysis with an iridium tridentate catalyst, prochiral N-phosphinoylimines
were hydrogenated with high enantioselectivity and reactivity. An outer-sphere
reaction model was proposed in this hydrogenation of CN bonds.



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The article was first published on 25 Jan 2021
Org. Chem. Front., 2021,8, 1223-1226
https://doi.org/10.1039/D0QO01286F
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Research Article


VISIBLE LIGHT-MEDIATED CROSS-COUPLING OF ELECTROPHILES: SYNTHESIS OF Α-AMINO
AMIDES FROM ISOCYANATES AND KETIMINES

Junli Zhu, Cancan Dai, Mengyue Ma, Yanni Yue and Xinyuan Fan

Cross-couplings between the electrophilic ketimines and isocyanates are achieved
via the visible light-mediated reactivity inversion of the ketimines, affording
the desired α-amino amides in high yields, with both metal and metal-free
systems.



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The article was first published on 18 Jan 2021
Org. Chem. Front., 2021,8, 1227-1232
https://doi.org/10.1039/D0QO01620A
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Research Article


BRØNSTED ACID-CATALYZED HOMOGENEOUS O–H AND S–H INSERTION REACTIONS UNDER METAL-
AND LIGAND-FREE CONDITIONS

Zhipeng Zhang, Zhiqin He, Yuxing Xie, Tiantong He, Yaofeng Fu, Yang Yu and Fei
Huang

The economical and accessible CF3SO3H successfully catalyzed homogeneous O–H and
S–H bond insertion reactions between hydroxyl compounds, thiols and diazo
compounds under metal- and ligand-free conditions.



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The article was first published on 15 Jan 2021
Org. Chem. Front., 2021,8, 1233-1242
https://doi.org/10.1039/D0QO01401J
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Research Article


ORGANOCATALYTIC REGIO-, DIASTEREO- AND ENANTIOSELECTIVE Γ-ADDITIONS OF
ISOXAZOL-5(4H)-ONES TO Β,Γ-ALKYNYL-Α-IMINO ESTERS FOR THE SYNTHESIS OF AXIALLY
CHIRAL TETRASUBSTITUTED Α-AMINO ALLENOATES

Fushuai Li, Shuai Liang, Yepeng Luan, Xuling Chen, Hanhui Zhao, Anqi Huang,
Pengfei Li and Wenjun Li

The chiral phosphoric acid catalyzed regio-, diastereo- and enantioselective
reaction of isoxazol-5(4H)-ones with β,γ-alkynyl-α-imino esters has been
developed.



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The article was first published on 20 Jan 2021
Org. Chem. Front., 2021,8, 1243-1248
https://doi.org/10.1039/D0QO01505A
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Research Article


TRIMERIC AND DIMERIC SESQUITERPENOIDS FROM ARTEMISIA ATROVIRENS AND THEIR
CYTOTOXICITIES

Li-Hua Su, Tian-Ze Li, Chang-An Geng, Yun-Bao Ma, Xiao-Yan Huang, Jin-Ping Wang,
Xue-Mei Zhang and Ji-Jun Chen

Two sesquiterpenoid trimers and two sesquiterpenoid dimers possessing
unprecedented scaffolds with a methylene-bridged connection were identified from
Artemisia atrovirens. Compound 3 showed obvious cytotoxicity against HepG2 and
Huh7 cell lines.



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The article was first published on 22 Jan 2021
Org. Chem. Front., 2021,8, 1249-1256
https://doi.org/10.1039/D0QO01615B
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Research Article


THEORETICAL STUDY OF RHODIUM- AND COBALT-CATALYZED DECARBOXYLATIVE
TRANSFORMATIONS OF ISOXAZOLONES: ORIGIN OF PRODUCT SELECTIVITY

Wei Rong, Tian Zhang, Ting Li and Juan Li

DFT calculations were performed to elucidate the origins of catalyst-controlled
product selectivity in the decarboxylative transformations of isoxazolones.



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The article was first published on 26 Jan 2021
Org. Chem. Front., 2021,8, 1257-1266
https://doi.org/10.1039/D0QO01498B
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Research Article


CASCADE INTRAMOLECULAR REARRANGEMENT/CYCLOADDITION OF NITROCYCLOPROPANE
CARBOXYLATES WITH ALKYNES/ALKENES: ACCESS TO UNCOMMON BI(HETERO)CYCLIC SYSTEMS

Rohit Kumar Varshnaya, Priyanka Singh, Navpreet Kaur and Prabal Banerjee

A straightforward approach for the one-pot synthesis of fused bi(hetero)cyclic
systems via cascade intramolecular rearrangement/cycloaddition reaction of
nitrocyclopropane carboxylates with substituted alkynes/alkenes has been
demonstrated.



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The article was first published on 21 Jan 2021
Org. Chem. Front., 2021,8, 1267-1274
https://doi.org/10.1039/D0QO01535K
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Research Article


PHTHALIMIDE-BASED-SSCF3 REAGENT FOR ENANTIOSELECTIVE DITHIOTRIFLUOROMETHYLATION

Wen-Chao Gao, Jianrong Liu and Xuefeng Jiang

A novel dithiotrifluoromethylation reagent phthN-SSCF3 was designed and prepared
for the incorporation of a SSCF3 unit into complex molecules and the
stereoselective construction of a SSCF3-tethered quaternary carbon center.



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The article was first published on 22 Jan 2021
Org. Chem. Front., 2021,8, 1275-1279
https://doi.org/10.1039/D1QO00001B
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Research Article


Α-C–H DIFLUOROALKYLATION OF ALKYL SULFOXIDES VIA INTERMOLECULAR PUMMERER
REACTION

Xin Huang, Weizhao Zhao, Yuchen Liang, Minghui Wang, Yaling Zhan, Yage Zhang,
Lichun Kong, Zhi-Xiang Wang and Bo Peng

A simple and practical intermolecular Pummerer reaction using difluoroenol silyl
ethers as nucleophiles is described. The protocol allows for highly efficient
α-difluoroalkylation of a wide spectrum of alkyl sulfoxides.



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The article was first published on 22 Jan 2021
Org. Chem. Front., 2021,8, 1280-1287
https://doi.org/10.1039/D0QO01513J
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Research Article


XANTHANOLTRIMER A–C: THREE XANTHANOLIDE SESQUITERPENE TRIMERS FROM THE FRUITS OF
XANTHIUM ITALICUM MORETTI ISOLATED BY HPLC-MS-SPE-NMR

Jiang Fu, Ya-Nan Wang, Shuang-Gang Ma, Li Li, Xiao-Jing Wang, Yong Li, Yun-Bao
Liu, Jing Qu and Shi-Shan Yu

Xanthanoltrimer A–C, first three xanthanolide sesquiterpene trimers from the
fruits of Xanthium italicum Moretti, were isolated by HPLC-MS-SPE-NMR.
Xanthanoltrimer A–C had an unprecedented 5/7/6/5/7/6/5/7 polycyclic scaffold.



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The article was first published on 26 Jan 2021
Org. Chem. Front., 2021,8, 1288-1293
https://doi.org/10.1039/D0QO01541E
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Highlight


MACROCYCLIC AND ACYCLIC SUPRAMOLECULAR ELEMENTS FOR CO-PRECIPITATION OF
SQUARE-PLANAR GOLD(III) TETRAHALIDE COMPLEXES

Cassandra C. Shaffer and Bradley D. Smith

Non-covalent interactions control the solid-state packing of AuX4− anions
(yellow circles) co-precipitated with different supramolecular elements.


From the themed collection: 2021 Organic Chemistry Frontiers Review-type
Articles

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The article was first published on 28 Jan 2021
Org. Chem. Front., 2021,8, 1294-1301
https://doi.org/10.1039/D0QO01562H
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Review Article


PHOTOEXCITED MOLECULAR PROBES FOR SELECTIVE AND REVERTIBLE IMAGING OF CELLULAR
REACTIVE OXYGEN SPECIES

Ying Wen, Zhiqing Long, Fangjun Huo and Caixia Yin

Redox homeostasis is key to maintaining the normal physiological status of
living cells.


From the themed collection: 2021 Organic Chemistry Frontiers Review-type
Articles

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The article was first published on 20 Jan 2021
Org. Chem. Front., 2021,8, 1302-1314
https://doi.org/10.1039/D0QO01260B
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Review Article


AN ELECTROCHEMICAL PERSPECTIVE ON THE ROLES OF LIGANDS IN THE MERGER OF
TRANSITION-METAL CATALYSIS AND ELECTROCHEMISTRY

Jun-Song Zhong, Yi Yu, Zhaojiang Shi and Ke-Yin Ye

A perspective on the roles of ligands in transition-metal catalysis under
electrochemical conditions is provided.


From the themed collection: 2021 Organic Chemistry Frontiers Review-type
Articles

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The article was first published on 28 Dec 2020
Org. Chem. Front., 2021,8, 1315-1328
https://doi.org/10.1039/D0QO01227K
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Review Article


THE OXA-MICHAEL REACTION IN THE SYNTHESIS OF 5- AND 6-MEMBERED OXYGEN-CONTAINING
HETEROCYCLES

Tauqir Ahmad and Nisar Ullah

In this review, we provide an updated account on the recent advances and
applications of oxa-Michael reaction in the synthesis 5- and 6-membered
monocyclic oxygen-containing heterocyclic compounds published in the literature
since 2013 to date.


From the themed collection: 2021 Organic Chemistry Frontiers Review-type
Articles

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The article was first published on 19 Jan 2021
Org. Chem. Front., 2021,8, 1329-1344
https://doi.org/10.1039/D0QO01312A
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Review Article


RECENT ADVANCES IN CASCADE RADICAL CYCLIZATION OF RADICAL ACCEPTORS FOR THE
SYNTHESIS OF CARBO- AND HETEROCYCLES

Jianhua Liao, Xiao Yang, Lu Ouyang, Yinlong Lai, Jiuzhong Huang and Renshi Luo

This review is devoted to highlighting main achievements in the development of
cascade radical cyclization of radical acceptors for the synthesis of carbo- and
heterocycles.


From the themed collection: FOCUS: Radical-involved chemical transformations

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The article was first published on 08 Jan 2021
Org. Chem. Front., 2021,8, 1345-1363
https://doi.org/10.1039/D0QO01453B
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Review Article


RECENT ADVANCES IN HYDRIDE TRANSFER-INVOLVED C(SP3)–H ACTIVATION REACTIONS

Xiao-De An and Jian Xiao

This review summarizes the recent progresses (2016–2020) in the hydride
transfer-enabled C(sp3)–H activation according to the reaction types,
categorized into the intramolecular/intermolecular C(sp3)–H functionalization,
and hydride reduction.


From the themed collection: 2021 Organic Chemistry Frontiers Review-type
Articles

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The article was first published on 07 Jan 2021
Org. Chem. Front., 2021,8, 1364-1383
https://doi.org/10.1039/D0QO01502D
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Correction


CORRECTION: FUSED AMBIPOLAR AZA-ISOINDIGOS WITH NIR ABSORPTION

Liping Yao, Danlei Zhu, Hailiang Liao, Sheik Haseena, Mahesh Kumar Ravva,
Shengyu Cong, Liuyuan Lan, Yazhou Wang, Zhengke Li, Lang Jiang and Wan Yue
From the themed collection: Recent Open Access Articles in Frontiers Journals

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The article was first published on 03 Mar 2021
Org. Chem. Front., 2021,8, 1384-1385
https://doi.org/10.1039/D1QO90017J
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