Grignard reagent dictated copper(I) phosphines catalyzed reductive coupling of diazo compounds: The chemistry beyond carbene generation

2021 ◽  
Author(s):  
Packirisamy Kuzhalmozhi Madarasi ◽  
Chinnappan Sivasankar
Keyword(s):  
Grignard Reagent ◽  
Diazo Compounds ◽  
Reductive Coupling

Carbon–Carbon Bond Construction: The Baran Synthesis of (+)-Chromazonarol

2015 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Grignard Reagent ◽  
Iron Catalyst ◽  
Alkyl Halide ◽  
Titanocene Dichloride ◽  
Secondary Amide ◽  
Reductive Coupling ◽  
Quaternary Centers ◽  
Carbon Carbon Bond ◽  
The University

Daniel J. Weix of the University of Rochester effected (Org. Lett. 2012, 14, 1476) the in situ reductive coupling of an alkyl halide 2 with an acid chloride 1 to deliver the ketone 3. André B. Charette of the Université de Montréal (not illustrated) developed (Nature Chem. 2012, 4, 228) an alternative route to ketones by the coupling of an organometallic with an in situ-activated secondary amide. Mahbub Alam and Christopher Wise of the Merck, Sharpe and Dohme UK chemical process group optimized (Org. Process Res. Dev. 2012, 16, 453) the opening of an epoxide 4 with a Grignard reagent 5. Ling Song of the Fujian Institute of Research on the Structure of Matter optimized (J. Org. Chem. 2012, 77, 4645) conditions for the 1,2-addition of a Grignard reagent (not illustrated) to a readily enolizable ketone. Wei-Wei Liao of Jilin University conceived (Org. Lett. 2012, 14, 2354) of an elegant assembly of highly functionalized quaternary centers, as illustrated by the conversion of 7 to 8. Antonio Rosales of the University of Granada and Ignacio Rodríguez-García of the University of Almería prepared (J. Org. Chem. 2012, 77, 4171) free radicals by reduction of an ozonide 9 in the presence of catalytic titanocene dichloride. In the absence of the acceptor 10, the dimer of the radical was obtained, presenting a simple alternative to the classic Kolbe coupling. Marc L. Snapper of Boston College found (Eur. J. Org. Chem. 2012, 2308) that the difficult ketone 12 could be methylenated following a modified Peterson protocol. Yoshito Kishi of Harvard University optimized (Org. Lett. 2012, 14, 86) the coupling of 15 with 16 to give 17. Masaharu Nakamura of Kyoto University devised (J. Org. Chem. 2012, 77, 1168) an iron catalyst for the coupling of 18 with 19. The specific preparation of trisubsituted alkenes is an ongoing challenge. Quanri Wang of Fudan University and Andreas Goeke of Givaudan Shanghai fragmented (Angew. Chem. Int. Ed. 2012, 51, 5647) the ketone 21 by exposure to 22 to give the macrolide 23 with high stereocontrol.

scholarly journals Transition-Metal-Free Reactions Between Boronic Acids and N-Sulfonylhydrazones or Diazo Compounds: Reductive Coupling Processes and Beyond

Synlett ◽  
2017 ◽  
Vol 28 (18) ◽  
pp. 2373-2389 ◽  
Author(s):  
Carlos Valdés ◽  
Miguel Paraja ◽  
Manuel Plaza
Keyword(s):  
Boronic Acids ◽  
Diazo Compounds ◽  
Primary Amines ◽  
Reductive Coupling ◽  
Cyclization Reactions ◽  
Metal Free ◽  
Bond Forming ◽  
Reductive Couplings ◽  
Cascade Processes ◽  
Coupling Processes

The metal-free reaction between diazo compounds and boronic acids has been established in recent years as a powerful C(sp3)–C bond-forming reaction. This account covers the recent advances in this area. First, the various synthetic applications of reactions with N-sulfonylhydrazones as a convenient source of diazo compounds is discussed. These transformations can be regarded as reductive couplings of carbonyl compounds. Also covered is the incorporation of other mild sources of diazo compounds in these reactions: diazotization of amines and oxidation of hydrazones. Finally, the development of sequential and cascade processes is presented.1 Introduction2 Early Work: Reactions Between Alkylboranes and Diazo Compounds or N-Sulfonylhydrazones2.1 Reactions Between Alkylboranes and Diazo Compounds2.2 Reactions Between Alkylboranes and N-Sulfonylhydrazones3 Reactions of N-Sulfonylhydrazones and Diazo Compounds with Aryl and Alkylboronic Acids3.1 Reactions of Arylboroxines with Diazo Compounds3.2 Reductive Couplings of N-Sulfonylhydrazones with Aryl- and Alkylboronic Acids3.3 Three-Component Reactions Between α-Halotosylhydrazones, Boronic Acids and Indoles4 Reactions of N-Tosylhydrazones with Alkenylboronic Acids5 Synthesis of Allenes by Reactions with Alkynyl N-Nosylhydrazones6 Reactions with Diazo Compounds Generated by Diazotization of Primary Amines7 Reactions with Diazo Compounds Generated by Oxidation of ­Hydrazones8 Reactions with Trimethylsilyldiazomethane9 Cascade Cyclization Reactions with γ- and δ-Cyano-N-tosylhydrazones10 Summary and Outlook

Metal-free Reductive Coupling of Biphenyl Tosylhydrazones with Phenols or Benzyl Alcohols

2017 ◽  
Vol 14 (10) ◽  
Author(s):  
Yang Liu ◽  
Ping Liu ◽  
Yan Liu ◽  
Yu Wei ◽  
Bin Dai
Keyword(s):  
Reductive Coupling ◽  
Benzyl Alcohols ◽  
Metal Free

Photoreaction of N-butyl 3,4-dimethoxy-6-nitrobenzamide with butylamine. A model study for lysine-directed photoaffinity labelling

1987 ◽  
Vol 52 (7) ◽  
pp. 1780-1785 ◽  
Author(s):  
Petr Kuzmič ◽  
Libuše Pavlíčková ◽  
Milan Souček
Keyword(s):  
Nitro Group ◽  
Aromatic Ring ◽  
Ultraviolet Irradiation ◽  
Title Compound ◽  
Reductive Coupling ◽  
Photoaffinity Labelling ◽  
Photolysis Rate ◽  
Model Study ◽  
A Minor

Ultraviolet irradiation of the title compound I in the presence of butylamine gave predominantly products of nucleophilic photosubstitution by the amine, i.e., nitroanilines IIa and IIb. Besides, small amounts of products of hydrolysis (phenol III) and reductive coupling (azoxybenzene IV) were also formed. Comparison of the overall photolysis rate of I with that of 3,4-dimethoxy-1-nitrobenzene (V) indicates a minor loss of reactivity, most probably due to some deviation from coplanarity of the activating nitro group and the aromatic ring.

New catalysts for the reduction of aromatic diazo compounds by alcohols to hydrocarbons

1983 ◽  
Vol 32 (4) ◽  
pp. 858-861 ◽  
Author(s):  
V. S. Lenenko ◽  
A. P. Borisov ◽  
V. D. Makhaev ◽  
E. I. Mysov ◽  
V. B. Shur ◽  
...  
Keyword(s):  
Diazo Compounds

Direct reductive coupling of nitroarenes and alcohols catalysed by Co–N–C/CNT@AC

2019 ◽  
Vol 21 (8) ◽  
pp. 2129-2137 ◽  
Author(s):  
Di Liu ◽  
Ping Yang ◽  
Hao Zhang ◽  
Minjie Liu ◽  
Wenfei Zhang ◽  
...  
Keyword(s):  
Solvent Free ◽  
Reductive Coupling ◽  
Solvent Free Conditions

Imines and amines were synthesized on Co–N–C/CNT@AC by the coupling of nitroarenes and alcohols under base- and solvent-free conditions.

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