perspective profiles in chemistry: a historical ...cnb.uran.ru/files/51c956507acc0.pdf · june 21,...

June 21, 2013

Volume 78, Issue 12

Pages 5817-6356

Perspective Profiles in Chemistry: A Historical Perspective on the National Organic Symposium

Edward E. Fenlon and Brian J. Myers

pp 5817–5831

Publication Date (Web): May 30, 2013 (Perspective)

DOI: 10.1021/jo302475j

Section:

History, Education, and Documentation

Featured Articles Nucleophile-Catalyzed Additions to Activated Triple Bonds. Protection of Lactams, Imides, and Nucleosides with MocVinyl and Related Groups

Laura Mola, Joan Font, Lluís Bosch, Joaquim Caner, Anna M. Costa, Gorka Etxebarría-Jardí, Oriol Pineda, David de Vicente, and Jaume Vilarrasa

pp 5832–5842

Publication Date (Web): May 28, 2013 (Featured Article)

DOI: 10.1021/jo4006409

Section:

General Organic Chemistry

Articles Double Reformatsky Reaction: Divergent Synthesis of δ-Hydroxy-β-ketoesters

Masahiro Mineno, Yasuhiro Sawai, Kazuaki Kanno, Naotaka Sawada, and Hideya Mizufune

pp 5843–5850

Publication Date (Web): June 4, 2013 (Article)

DOI: 10.1021/jo400408t

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Section:


Stereochemical Outcome of Copper-Catalyzed C–H Insertion Reactions. An Experimental and Theoretical Study

Gonzalo Jiménez-Osés, Eugenio Vispe, Marta Roldán, Sergio Rodríguez-Rodríguez, Pilar López-Ram-de-Viu, Luis Salvatella, José A. Mayoral, and José M. Fraile

pp 5851–5857

Publication Date (Web): May 23, 2013 (Article)

DOI: 10.1021/jo400415b

Section:

Physical Organic Chemistry

Straightforward Access to Spisulosine and 4,5-Dehydrospisulosine Stereoisomers: Probes for Profiling Ceramide Synthase Activities in Intact Cells

José Luis Abad, Ingrid Nieves, Pedro Rayo, Josefina Casas, Gemma Fabriàs, and Antonio Delgado

pp 5858–5866


DOI: 10.1021/jo400440z

Section:

Biomolecules and Their Synthetic Analogs

8-Alkoxy- and 8-Aryloxy-BODIPYs: Straightforward Fluorescent Tagging of Alcohols and Phenols

- - , César F. A. Gómez-Durán, Jorge Bañuelos, Iñigo López Arbeloa, Keith H. Pannell, Alejandro J. Metta-Magaña, and Eduardo Peña-Cabrera

pp 5867–5877


DOI: 10.1021/jo400417h

Section:

Organometallic and Organometalloidal Compounds

Synthesis of Substituted 3-Iodocoumarins and 3-Iodobutenolides via Electrophilic Iodocyclization of Ethoxyalkyne Diols

Maddi Sridhar Reddy, Nuligonda Thirupathi, Madala Hari Babu, and Surendra Puri

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pp 5878–5888


DOI: 10.1021/jo400499r

Section:

Heterocyclic Compounds (One Hetero Atom)

Chromophores Arranged as “Magnetic Meta Atoms”: Building Blocks for Molecular Metamaterials

Heinz Langhals and Alexander Hofer

pp 5889–5897


DOI: 10.1021/jo4005662

Section:

Optical, Electron, and Mass Spectroscopy and Other Related Properties

Reaction Pathways for the Thermal Decomposition of Methyl Butanoate Mohamad Akbar Ali and Angela Violi

pp 5898–5908


DOI: 10.1021/jo400569d

Section:

Electrochemical, Radiational, and Thermal Energy Technology

Reactions of the Cumyloxyl and Benzyloxyl Radicals with Tertiary Amides. Hydrogen Abstraction Selectivity and the Role of Specific Substrate-Radical Hydrogen Bonding

Michela Salamone, Michela Milan, Gino A. DiLabio, and Massimo Bietti

pp 5909–5917


DOI: 10.1021/jo400535u

Section:


A Method for Synthesis of Homoallylic Bromide Wenke Qi, Peipei Wang, Liyuan Fan, and Songlin Zhang

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pp 5918–5924


DOI: 10.1021/jo400580n

Section:


Twisting-Based Spectroscopic Measure of Solvent Polarity: The PT Scale Wei-Jen Lo, Yi-Hui Chen, and Kuangsen Sung

pp 5925–5931

Publication Date (Web): April 23, 2013 (Article)

DOI: 10.1021/jo400586w

Section:


Palladium-Catalyzed Chelation-Assisted Aromatic C–H Nitration: Regiospecific Synthesis of Nitroarenes Free from the Effect of the Orientation Rules

Wei Zhang, Shaojie Lou, Yunkui Liu, and Zhenyuan Xu

pp 5932–5948


DOI: 10.1021/jo400594j

Section:

Benzene, Its Derivatives, and Condensed Benzenoid Compounds

A Predictably Selective Nitration of Olefin with Fe(NO3)3 and TEMPO Togati Naveen, Soham Maity, Upendra Sharma, and Debabrata Maiti

pp 5949–5954


DOI: 10.1021/jo400598p

Section:


Telescoped Approach to Aryl Hydroxymethylation in the Synthesis of a Key Pharmaceutical Intermediate

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Catherine N. Slattery, Rebecca E. Deasy, and Anita R. Maguire , Michael E. Kopach, Utpal K. Singh, Mark D. Argentine, William G. Trankle, and Roger Brian Scherer , Humphrey Moynihan

pp 5955–5963


DOI: 10.1021/jo400647t

Section:


Synthesis of Triazole-Linked Oligonucleotides with High Affinity to DNA Complements and an Analysis of Their Compatibility with Biosystems

Anna M. Varizhuk, Dmitry N. Kaluzhny, Roman A. Novikov, Alexandr O. Chizhov, Igor P. Smirnov, Andrey N. Chuvilin, Olga N. Tatarinova, Gleb Y. Fisunov, Galina E. Pozmogova, and Vladimir L. Florentiev

pp 5964–5969


DOI: 10.1021/jo400651k

Section:

Biochemical Genetics

Highly Stereocontrolled Total Synthesis of β-d-Mannosyl Phosphomycoketide: A Natural Product from Mycobacterium tuberculosis

Nan-Sheng Li, Louise Scharf, Erin J. Adams, and Joseph A. Piccirilli

pp 5970–5986


DOI: 10.1021/jo4006602

Section:

Carbohydrates

An Alternative Role for Acetylenes: Activation of Fluorobenzenes toward Nucleophilic Aromatic Substitution

Nicholas P. Bizier, Jay Wm. Wackerly, Eric D. Braunstein, Mengfei Zhang, Stephen T. Nodder, Stephen M. Carlin, and Jeffrey L. Katz

pp 5987–5998


DOI: 10.1021/jo400668v

Section:

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Hydroxyphosphinylation Reaction of 3-Cyclopropylideneprop-2-en-1-ones via C–P σ-Bond Cleavage

Maozhong Miao, Jian Cao, Xian Huang, and Luling Wu

pp 5999–6007


DOI: 10.1021/jo400610q

Section:


In Search of Catalytic Antioxidants—(Alkyltelluro)phenols, (Alkyltelluro)resorcinols, and Bis(alkyltelluro)phenols

Jia-fei Poon, Vijay P. Singh, and Lars Engman

pp 6008–6015


DOI: 10.1021/jo400703w

Section:


Transition-Metal-Free Arylations via Photogenerated Triplet 4-Alkyl- and 4-Trimethylsilylphenyl Cations

Hisham Qrareya, Carlotta Raviola, Stefano Protti, Maurizio Fagnoni, and Angelo Albini

pp 6016–6024


DOI: 10.1021/jo4007046

Section:


Synthesis of 6-(Trifluoromethyl)phenanthridines via Palladium-Catalyzed Tandem Suzuki/C–H Arylation Reactions

Wen-Ying Wang, Xia Feng, Bo-Lun Hu, Chen-Liang Deng, and Xing-Guo Zhang

pp 6025–6030


DOI: 10.1021/jo4007255

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Solution State Conformational Preferences of Dipeptides Derived from N-Aminoazetidinecarboxylic Acid: An Assessment of the Hydrazino Turn

Amandine Altmayer-Henzien, Valérie Declerck, Denis Merlet, Jean-Pierre Baltaze, Jonathan Farjon, Régis Guillot, and David J. Aitken

pp 6031–6039


DOI: 10.1021/jo400736t

Section:


Spectroscopy of Protonated Tetraphenylporphyrins with Amino/Carbomethoxy Substituents: Hyperporphyrin Effects and Evidence for a Monoprotonated Porphyrin

Alexander B. Rudine, Brian D. DelFatti, and Carl C. Wamser

pp 6040–6049


DOI: 10.1021/jo400742f

Section:


Iron-Catalyzed Oxidative Tandem Reactions with TEMPO Oxoammonium Salts: Synthesis of Dihydroquinazolines and Quinolines

pp 6050–6064


DOI: 10.1021/jo4007199

Section:

Heterocyclic Compounds (More than One Hetero Atom)

Direct Synthesis of 2,5-Disubstituted Oxazoles through an Iodine-Catalyzed Decarboxylative Domino Reaction

Wei Xu, Ulrich Kloeckner, and Boris J. Nachtsheim

pp 6065–6074

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DOI: 10.1021/jo400753n

Section:


A Study of Exocyclic Radical Reductions of Polysubstituted Tetrahydropyrans

François Godin, Michel Prévost, Frédérick Viens, Philippe Mochirian, Jean-François Brazeau, Serge I. Gorelsky, and Yvan Guindon

pp 6075–6103


DOI: 10.1021/jo400721e

Section:


Pd(II)-Catalyzed Aminotetrazole-Directed Ortho-Selective Halogenation of Arenes

Pradeep Sadhu, Santhosh Kumar Alla, and Tharmalingam Punniyamurthy

pp 6104–6111


DOI: 10.1021/jo400755q

Section:


Reductive Carbonylation of Aryl Halides Employing a Two-Chamber Reactor: A Protocol for the Synthesis of Aryl Aldehydes Including 13C- and D-Isotope Labeling

Signe Korsager, Rolf H. Taaning, Anders T. Lindhardt, and Troels Skrydstrup

pp 6112–6120


DOI: 10.1021/jo400741t

Section:


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Coumarin- and Rhodamine-Fused Deep Red Fluorescent Dyes: Synthesis, Photophysical Properties, and Bioimaging in Vitro

Jianhong Chen, Weimin Liu, Bingjiang Zhou, Guangle Niu, Hongyan Zhang, Jiasheng Wu, Ying Wang, Weigang Ju, and Pengfei Wang

pp 6121–6130


DOI: 10.1021/jo400783x

Section:

Biochemical Methods

N–O Tethered Carbenoid Cyclopropanation Facilitates the Synthesis of a Functionalized Cyclopropyl-Fused Pyrrolidine

Dimpy Kalia, Gökce Merey, Min Guo, and Herman O. Sintim

pp 6131–6142


DOI: 10.1021/jo400788a

Section:


Synthesis of Highly Substituted Cryptophane Derivatives Thierry Brotin, Dominique Cavagnat, Erwann Jeanneau, and Thierry Buffeteau

pp 6143–6153


DOI: 10.1021/jo4007738

Section:


Transannular Reductive Rearrangement of α-Amino Ketones: Construction of Aza-tricyclic Frameworks of Several Alkaloids

Jian Zhang, Yong-Qiang Wang, Xin-Wei Wang, and Wei-Dong Z. Li

pp 6154–6162


DOI: 10.1021/jo4007943

Section:

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Alkaloids

Palladium-Catalyzed Direct C–H Arylation of Cyclic Enaminones with Aryl Iodides

Yi-Yun Yu, Lei Bi, and Gunda I. Georg

pp 6163–6169


DOI: 10.1021/jo400830t

Section:


Nanocrystalline and Reusable ZnO Catalyst for the Assembly of Densely Functionalized 4H-Chromenes in Aqueous Medium via One-Pot Three Component Reactions: A Greener “NOSE” Approach

Partha Pratim Ghosh and Asish R. Das

pp 6170–6181


DOI: 10.1021/jo400763z

Section:


Diastereoselective Synthesis of Tetrahydrofurans by Lewis Acid Catalyzed Intermolecular Carbenoid–Carbonyl Reaction–Cycloaddition Sequences: Unusual Diastereoselectivity of Lewis Acid Catalyzed Cycloadditions

Yuta Hashimoto, Kennosuke Itoh, Akikazu Kakehi, Motoo Shiro, and Hiroyuki Suga

pp 6182–6195


DOI: 10.1021/jo400858u

Section:


Synthesis of 2-Aryl-3-trifluoromethylquinolines Using (E)-Trimethyl(3,3,3-trifluoroprop-1-enyl)silane

Masaaki Omote, Miyuu Tanaka, Miki Tanaka, Akari Ikeda, Atsushi Tarui, Kazuyuki Sato, and Akira Ando

pp 6196–6201

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DOI: 10.1021/jo400859s

Section:


Synthesis of Triphenylene Derivatives by Rhodium-Catalyzed [2 + 2 + 2] Cycloaddition: Application to the Synthesis of Highly Fluorescent Triphenylene-Based Long Ladder Molecules

Koichi Murayama, Yayoi Sawada, Keiichi Noguchi, and Ken Tanaka

pp 6202–6210


DOI: 10.1021/jo4008892

Section:

Dyes, Organic Pigments, Fluorescent Brighteners, and Photographic Sensitizers

Photoinduced Reactions of para-Quinones with Bicyclopropylidene Leading to Diverse Polycyclic Compounds with Spirocyclopropanes

Wei Wang, Wen-Jie Zhang, Lei Wang, Ching Kheng Quah, Hoong-Kun Fun, Jian-Hua Xu, and Yan Zhang

pp 6211–6222


DOI: 10.1021/jo4008767

Section:


Divergent NHC-Catalyzed Oxidative Transformations of 3-Bromoenal: Selective Synthesis of 2H-Pyran-2-ones and Chiral Dihydropyranones

Gang Wang, Xia Chen, Gaohan Miao, Weijun Yao, and Cheng Ma

pp 6223–6232


DOI: 10.1021/jo400950j

Section:


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Synthesis of Cyclopentenimines from N-Allyl Ynamides via a Tandem Aza-Claisen Rearrangement–Carbocyclization Sequence

Xiao-Na Wang, Gabrielle N. Winston-McPherson, Mary C. Walton, Yu Zhang, Richard P. Hsung, and Kyle A. DeKorver

pp 6233–6244


DOI: 10.1021/jo400960e

Section:


Synthesis of a Leucomitosane via a Diastereoselective Radical Cascade François Brucelle and Philippe Renaud

pp 6245–6252


DOI: 10.1021/jo4009904

Section:

Alkaloids

A Model System for the Synthesis of Complanadine Alkaloids by “Diverted Kondrat’eva” Oxazole–Olefin Cycloaddition

Mario Uosis-Martin, G. Dan Pantoş, Mary F. Mahon, and Simon E. Lewis

pp 6253–6263


DOI: 10.1021/jo401014n

Section:

Alkaloids

Stereochemistry of 1,5-Benzothiazepin-4-one S-Oxide: Insight into the Stereogenic Elements at the Sulfur Atom and Axis

Hidetsugu Tabata, Tetsuya Yoneda, Tetsuta Oshitari, Hideyo Takahashi, and Hideaki Natsugari

pp 6264–6270


DOI: 10.1021/jo401020y

Section:

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Notes Synthesis and Structure of Bull’s Horn-Shaped Oligothienoacene with Seven Fused Thiophene Rings

Huiliang Sun, Jianwu Shi, Zilong Zhang, Sheng Zhang, Zhaoli Liang, Shisheng Wan, Yanxiang Cheng, and Hua Wang

pp 6271–6275

Publication Date (Web): May 20, 2013 (Note)

DOI: 10.1021/jo4002036

Section:


An Organocatalyst Bearing Stereogenic Carbon and Sulfur Centers as an Efficient Promoter for Enantioselective Hydrosilylation of 1,4-Benzooxazines

Xiang-Wei Liu, Chao Wang, Yan Yan, Yong-Qiang Wang, and Jian Sun

pp 6276–6280


DOI: 10.1021/jo400187e

Section:


Syntheses and Determination of Absolute Configurations and Biological Activities of the Enantiomers of the Longtailed Mealybug Pheromone

Remya Ramesh, Pandrangi Siva Swaroop, Rajesh G. Gonnade, Choppari Thirupathi, Rebeccah A. Waterworth, Jocelyn G. Millar, and D. Srinivasa Reddy

pp 6281–6284


DOI: 10.1021/jo400491n

Section:


Synthesis and Functionalization of BF2-Complexes of meso-Free 25-Oxasmaragdyrin

Hemanta Kalita, Way-Zen Lee, and Mangalampalli Ravikanth

pp 6285–6290

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DOI: 10.1021/jo400540u

Section:

Inorganic Chemicals and Reactions

Concise Synthesis of the Isothiourea Organocatalysts Homobenzotetramisole and Derivatives

Beatrice Ranieri, Omar Robles, and Daniel Romo

pp 6291–6296


DOI: 10.1021/jo400603n

Section:


Regiochemistry Discoveries in the Use of Isoxazole as a Handle for the Rapid Construction of an All-Carbon Macrocyclic Precursor in the Synthetic Studies of Celastrol

Thomas M. Kaiser, Jinhua Huang, and Jiong Yang

pp 6297–6302


DOI: 10.1021/jo400612v

Section:


Thia-Prins Bicyclization Approach for the Stereoselective Synthesis of Dithia- and Azathia-Bicycles

B. V. Subba Reddy, A. Venkateswarlu, Prashant Borkar, J. S. Yadav, M. Kanakaraju, A. C. Kunwar, and B. Sridhar

pp 6303–6308


DOI: 10.1021/jo400680w

Section:


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Palladium-Catalyzed Intermolecular Aminoacetoxylation of Alkenes and the Influence of PhI(OAc)2 on Aminopalladation Stereoselectivity

Claudio Martínez, Yichen Wu, Adam B. Weinstein, Shannon S. Stahl, Guosheng Liu, and Kilian Muñiz

pp 6309–6315


DOI: 10.1021/jo400671q

Section:


Synthesis for the Mesomer and Racemate of Thiophene-Based Double Helicene under Irradiation

Xinming Liu, Panpan Yu, Li Xu, Juanjuan Yang, Jianwu Shi, Zhihua Wang, Yanxiang Cheng, and Hua Wang

pp 6316–6321


DOI: 10.1021/jo400691s

Section:


Asymmetric Organocatalytic Cyclopropanation of Cinnamone Derivatives with Stabilized Sulfonium Ylides

Jing Wang, Xiaohua Liu, Shunxi Dong, Lili Lin, and Xiaoming Feng

pp 6322–6327


DOI: 10.1021/jo400743b

Section:

Alicyclic Compounds

Deoxygenation of Sulfoxides to Sulfides with Thionyl Chloride and Triphenylphosphine: Competition with the Pummerer Reaction

Yujin Jang, Kyoung Tae Kim, and Heung Bae Jeon

pp 6328–6331


DOI: 10.1021/jo4008157

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Palladium-Catalyzed Z-Selective Oxidative Amination of ortho-Substituted Primary Anilines with Olefins under an Open Air Atmosphere

Yohei Mizuta, Kaoru Yasuda, and Yasushi Obora

pp 6332–6337

Publication Date (Web): June 4, 2013 (Note)

DOI: 10.1021/jo4010734

Section:


Asymmetric Total Synthesis of Fusarentin 6-Methyl Ether and Its Biomimetic Transformation into Fusarentin 6,7-Dimethyl Ether, 7-O-Demethylmonocerin, and (+)-Monocerin

Bowen Fang, Xingang Xie, Changgui Zhao, Peng Jing, Huilin Li, Zhengshen Wang, Jixiang Gu, and Xuegong She

pp 6338–6343


DOI: 10.1021/jo400760q

Section:


Fine-Tuning the Oxidative Ability of Persistent Radicals: Electrochemical and Computational Studies of Substituted 2-Pyridylhydroxylamines

Justin A. Bogart, Heui Beom Lee, Michael A. Boreen, Minsik Jun, and Eric J. Schelter

pp 6344–6349


DOI: 10.1021/jo400944r

Section:


A Chiral Ruthenium-Monophosphine Catalyst for Asymmetric Addition of Arylboronic Acids to Aryl Aldehydes

Ke Li, Naifu Hu, Renshi Luo, Weicheng Yuan, and Wenjun Tang

pp 6350–6355

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DOI: 10.1021/jo400850m

Section:


Additions and Corrections Correction to Palladium-Catalyzed Cascade Reactions of 1-(3-Arylprop-2-ynyloxy)-2-bromo Benzene Derivatives with Organoboron Compounds

Antonio Arcadi, Federico Blesi, Sandro Cacchi, Giancarlo Fabrizi, Antonella Goggiamani, and Fabio Marinelli

pp 6356–6356

Publication Date (Web): June 10, 2013 (Addition/Correction)

DOI: 10.1021/jo4011975

Section:


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