Literature DB >> 31243998

Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts.

Daniel Kaiser, Immo Klose, Rik Oost, James Neuhaus, Nuno Maulide1.   

Abstract

Organosulfur compounds have long played a vital role in organic chemistry and in the development of novel chemical structures and architectures. Prominent among these organosulfur compounds are those involving a sulfur(IV) center, which have been the subject of countless investigations over more than a hundred years. In addition to a long list of textbook sulfur-based reactions, there has been a sustained interest in the chemistry of organosulfur(IV) compounds in recent years. Of particular interest within organosulfur chemistry is the ease with which the synthetic chemist can effect a wide range of transformations through either bond formation or bond cleavage at sulfur. This review aims to cover the developments of the past decade in the chemistry of organic sulfur(IV) molecules and provide insight into both the wide range of reactions which critically rely on this versatile element and the diverse scaffolds that can thereby be synthesized.

Entities:  

Year:  2019        PMID: 31243998      PMCID: PMC6661881          DOI: 10.1021/acs.chemrev.9b00111

Source DB:  PubMed          Journal:  Chem Rev        ISSN: 0009-2665            Impact factor:   60.622


  386 in total

1.  Palladium-assisted "aromatic metamorphosis" of dibenzothiophenes into triphenylenes.

Authors:  Dhananjayan Vasu; Hideki Yorimitsu; Atsuhiro Osuka
Journal:  Angew Chem Int Ed Engl       Date:  2015-05-04       Impact factor: 15.336

2.  Synthesis of N-alkylated 2-pyridones through Pummerer type reactions of activated sulfoxides and 2-fluoropyridine derivatives.

Authors:  Gang Hu; Jiaxi Xu; Pingfan Li
Journal:  Org Biomol Chem       Date:  2018-06-06       Impact factor: 3.876

3.  Pd-Catalyzed Conversion of Aryl Iodides to Sulfonyl Fluorides Using SO2 Surrogate DABSO and Selectfluor.

Authors:  Ariana L Tribby; Ismeraí Rodríguez; Shamira Shariffudin; Nicholas D Ball
Journal:  J Org Chem       Date:  2017-02-09       Impact factor: 4.354

4.  Integrated electrochemical-chemical oxidation mediated by alkoxysulfonium ions.

Authors:  Yosuke Ashikari; Toshiki Nokami; Jun-ichi Yoshida
Journal:  J Am Chem Soc       Date:  2011-07-18       Impact factor: 15.419

5.  Metal-Free Trifluoromethylation of Indazoles.

Authors:  Payel Ghosh; Susmita Mondal; Alakananda Hajra
Journal:  J Org Chem       Date:  2018-10-22       Impact factor: 4.354

6.  Direct synthesis of fluorinated heteroarylether bioisosteres.

Authors:  Qianghui Zhou; Alessandro Ruffoni; Ryan Gianatassio; Yuta Fujiwara; Eran Sella; Doron Shabat; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2013-03-04       Impact factor: 15.336

7.  Catalytic Asymmetric Synthesis of Fluoroalkyl-Containing Compounds by Three-Component Photoredox Chemistry.

Authors:  Jiajia Ma; Xiulan Xie; Eric Meggers
Journal:  Chemistry       Date:  2017-12-04       Impact factor: 5.236

8.  Visible-Light-Driven Photocatalytic Activation of Inert Sulfur Ylides for 3-Acyl Oxindole Synthesis.

Authors:  Xu-Dong Xia; Liang-Qiu Lu; Wen-Qiang Liu; Dong-Zhen Chen; Yu-Han Zheng; Li-Zhu Wu; Wen-Jing Xiao
Journal:  Chemistry       Date:  2016-04-26       Impact factor: 5.236

9.  Switchable Decarboxylative Heck-Type Reaction and Oxo-alkylation of Styrenes with N-Hydroxyphthalimide Esters under Photocatalysis.

Authors:  Zi-Hao Xia; Chun-Lin Zhang; Zhong-Hua Gao; Song Ye
Journal:  Org Lett       Date:  2018-06-04       Impact factor: 6.005

10.  Ring-Closing Synthesis of Dibenzothiophene Sulfonium Salts and Their Use as Leaving Groups for Aromatic 18F-Fluorination.

Authors:  Thibault Gendron; Kerstin Sander; Klaudia Cybulska; Laure Benhamou; Pak Kwan Brian Sin; Aqsa Khan; Michael Wood; Michael J Porter; Erik Årstad
Journal:  J Am Chem Soc       Date:  2018-08-22       Impact factor: 15.419

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  34 in total

Review 1.  Catalytic, Enantioselective Sulfenofunctionalization of Alkenes: Development and Recent Advances.

Authors:  Anastassia Matviitsuk; Jesse L Panger; Scott E Denmark
Journal:  Angew Chem Int Ed Engl       Date:  2020-08-18       Impact factor: 15.336

2.  Tunable Aziridinium Ylide Reactivity: Non-covalent Interactions Enable Divergent Product Outcomes.

Authors:  Kate A Nicastri; Soren Zappia; Jared C Pratt; Julia M Duncan; Ilia A Guzei; Israel Fernández; Jennifer M Schomaker
Journal:  ACS Catal       Date:  2022-01-11       Impact factor: 13.084

Review 3.  Synthesis and applications of sodium sulfinates (RSO2Na): a powerful building block for the synthesis of organosulfur compounds.

Authors:  Raju Jannapu Reddy; Arram Haritha Kumari
Journal:  RSC Adv       Date:  2021-03-01       Impact factor: 3.361

4.  Catalytic Reductive Carbene Transfer Reactions.

Authors:  Christopher Uyeda; Annah E Kalb
Journal:  Chem Catal       Date:  2022-02-04

5.  Selective Oxidation of Polysulfide Latexes to Produce Polysulfoxide and Polysulfone in a Waterborne Environment.

Authors:  Lorena Infante Teixeira; Katharina Landfester; Héloïse Thérien-Aubin
Journal:  Macromolecules       Date:  2021-04-08       Impact factor: 5.985

6.  Site-Selective Late-Stage Aromatic [18 F]Fluorination via Aryl Sulfonium Salts.

Authors:  Peng Xu; Da Zhao; Florian Berger; Aboubakr Hamad; Jens Rickmeier; Roland Petzold; Mykhailo Kondratiuk; Kostiantyn Bohdan; Tobias Ritter
Journal:  Angew Chem Int Ed Engl       Date:  2019-12-12       Impact factor: 15.336

7.  Decatungstate-Catalyzed C(sp3)-H Sulfinylation: Rapid Access to Diverse Organosulfur Functionality.

Authors:  Patrick J Sarver; Noah B Bissonnette; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2021-06-23       Impact factor: 15.419

8.  Divergent reactivity of sulfinates with pyridinium salts based on one- versus two-electron pathways.

Authors:  Myojeong Kim; Euna You; Seongjin Park; Sungwoo Hong
Journal:  Chem Sci       Date:  2021-03-31       Impact factor: 9.825

9.  Unexpected Substituent Effects in Spiro-Compound Formation: Steering N-Aryl Propynamides and DMSO toward Site-Specific Sulfination in Quinolin-2-ones or Spiro[4,5]trienones.

Authors:  Xiaoxian Li; Yuanxun Wang; Yaxin Ouyang; Zhenyang Yu; Beibei Zhang; Jingran Zhang; Haofeng Shi; Han Zuilhof; Yunfei Du
Journal:  J Org Chem       Date:  2021-06-29       Impact factor: 4.354

10.  Aziridine synthesis by coupling amines and alkenes via an electrogenerated dication.

Authors:  Dylan E Holst; Diana J Wang; Min Ji Kim; Ilia A Guzei; Zachary K Wickens
Journal:  Nature       Date:  2021-06-22       Impact factor: 69.504

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