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Literature DB >> 26236153

Alkyl Sulfinates: Formal Nucleophiles for Synthesizing TosMIC Analogs.

J Armando Lujan-Montelongo¹, Angel Ojeda Estevez², Fraser F Fleming².

Abstract

Alkyl sulfinates function as formal nucleophiles in Mannich-type reactions to give sulfonyl formamides, which are readily dehydrated to the corresponding sulfonylmethyl isonitriles. The efficient, two-step synthesis provides a general route to sulfonylmethyl isonitriles from readily available methyl sulfinates or thiols. Mechanistic analysis reveals that the unusual nucleophlicity of the alkyl sulfinates arises from the in situ release of sulfinic acids.

Entities: Chemical Disease Gene

Keywords: Isocyanides; Isonitriles; Mannich reaction; Nucleophilic addition; Sulfinates; Umpolung

Year: 2015 PMID： 26236153 PMCID： PMC4520545 DOI： 10.1002/ejoc.201403615

Source DB: PubMed Journal: European J Org Chem ISSN： 1099-0690

12 in total

1. Highly active mononuclear NAC-gold(I) catalysts.

Authors: Maria Camila Blanco Jaimes; Constantin R N Böhling; Juan Manuel Serrano-Becerra; A Stephen K Hashmi
Journal: Angew Chem Int Ed Engl Date: 2013-06-20 Impact factor: 15.336

2. Synthesis of constrained alpha-amino acid derivatives via ring-closing olefin metathesis.

Authors: S Kotha; N Sreenivasachary
Journal: Bioorg Med Chem Lett Date: 1998-02-03 Impact factor: 2.823

3. Regioselective formation of saturated abnormal NHC-gold(I) complexes by [3+2] cycloaddition of azomethine ylides and isonitrile gold(I) complexes.

Authors: A Stephen K Hashmi; Dominic Riedel; Matthias Rudolph; Frank Rominger; Thomas Oeser
Journal: Chemistry Date: 2012-02-29 Impact factor: 5.236

4. Copper/silver-mediated cascade reactions for the construction of 2-sulfonylbenzo[b]furans from trans-2-hydroxycinnamic acids and sodium sulfinates.

Authors: Hong-Shuang Li; Gang Liu
Journal: J Org Chem Date: 2013-12-26 Impact factor: 4.354

5. Nucleophilicity and nucleofugality of phenylsulfinate (PhSO(2)(-)): a key to understanding its ambident reactivity.

Authors: Mahiuddin Baidya; Shinjiro Kobayashi; Herbert Mayr
Journal: J Am Chem Soc Date: 2010-04-07 Impact factor: 15.419

6. Iodine-catalyzed regioselective 2-sulfonylation of indoles with sodium sulfinates.

Authors: Fuhong Xiao; Hui Chen; Hao Xie; Shuqing Chen; Luo Yang; Guo-Jun Deng
Journal: Org Lett Date: 2013-12-11 Impact factor: 6.005

7. Arylation of lithium sulfinates with diaryliodonium salts: a direct and versatile access to arylsulfones.

Authors: Natalie Umierski; Georg Manolikakes
Journal: Org Lett Date: 2013-09-18 Impact factor: 6.005

8. Catalytic Isonitrile Insertions and Condensations Initiated by RNC-X Complexation.

Authors: Suravi Chakrabarty; Shruti Choudhary; Arpit Doshi; Fa-Qiang Liu; Rishabh Mohan; Manasa P Ravindra; Dhruv Shah; Xun Yang; Fraser F Fleming
Journal: Adv Synth Catal Date: 2014-06-20 Impact factor: 5.837

9. Metal-free synthesis of diaryl sulfones from arylsulfinic acid salts and diaryliodonium salts.

Authors: Natalie Umierski; Georg Manolikakes
Journal: Org Lett Date: 2012-12-19 Impact factor: 6.005

10. An expeditious entry to benzylic and allylic sulfones through byproduct-catalyzed reaction of alcohols with sulfinyl chlorides.

Authors: Hai-Hua Li; De-Jun Dong; Yin-Huan Jin; Shi-Kai Tian
Journal: J Org Chem Date: 2009-12-18 Impact factor: 4.354

7 in total

Alkyl Sulfinates: Formal Nucleophiles for Synthesizing TosMIC Analogs.

1. Highly active mononuclear NAC-gold(I) catalysts.

2. Synthesis of constrained alpha-amino acid derivatives via ring-closing olefin metathesis.

3. Regioselective formation of saturated abnormal NHC-gold(I) complexes by [3+2] cycloaddition of azomethine ylides and isonitrile gold(I) complexes.

4. Copper/silver-mediated cascade reactions for the construction of 2-sulfonylbenzo[b]furans from trans-2-hydroxycinnamic acids and sodium sulfinates.

5. Nucleophilicity and nucleofugality of phenylsulfinate (PhSO(2)(-)): a key to understanding its ambident reactivity.

6. Iodine-catalyzed regioselective 2-sulfonylation of indoles with sodium sulfinates.

7. Arylation of lithium sulfinates with diaryliodonium salts: a direct and versatile access to arylsulfones.

8. Catalytic Isonitrile Insertions and Condensations Initiated by RNC-X Complexation.

9. Metal-free synthesis of diaryl sulfones from arylsulfinic acid salts and diaryliodonium salts.

10. An expeditious entry to benzylic and allylic sulfones through byproduct-catalyzed reaction of alcohols with sulfinyl chlorides.

1. Alkenyl Isocyanide Conjugate Additions: A Rapid Route to γ-Carbolines.

2. Asmic: An Exceptional Building Block for Isocyanide Alkylations.

3. K₂CO₃-Catalyzed Rapid Conversion of N-Sulfonylhydrazones to Sulfinates.

4. Tough and Functional Cross-linked Bioplastics from Sheep Wool Keratin.

5. Synthesis of N^β-Protected Amino Sulfenyl Methyl Formamides and Sulfonyl Methyl Formamides: A Simple Protocol.

6. An expeditious and efficient bromomethylation of thiols: enabling bromomethyl sulfides as useful building blocks.

Review 7. Recent Advances in the Synthesis of Oxazole-Based Molecules via van Leusen Oxazole Synthesis.