Nickel Catalysis in a High Speed Ball Mill: A Recyclable Mechanochemical Method for Producing Substituted Cyclooctatetraene Compounds

A solvent-free, nickel-catalyzed [2 + 2+2 + 2] cycloaddition of alkynes to synthesize substituted cyclooctatetraene (COT) derivatives has been developed. This mechanochemical approach takes advantage of the frictional energy created by reusable nickel pellets, which also act as the catalyst. In contrast to solution chemistry, the major products are cyclooctatetraene isomers rather than substituted benzenes.

[1]  L. Takács.  M. Carey Lea, the first mechanochemist , 2004 .

[2]  Bernd Ondruschka,et al.  Energetic assessment of the Suzuki–Miyaura reaction: a curtate life cycle assessment as an easily understandable and applicable tool for reaction optimization , 2009 .

[3]  A. Kwade,et al.  Effect of Reaction Parameters on the Synthesis of 5-Arylidene Barbituric Acid Derivatives in Ball Mills , 2015 .

[4]  B. Ondruschka,et al.  The Suzuki−Miyaura Reaction under Mechanochemical Conditions§ , 2009 .

[5]  T. Friščić,et al.  Mechanosynthesis of pharmaceutically relevant sulfonyl-(thio)ureas. , 2014, Chemical communications.

[6]  P. Wender,et al.  Rhodium dinaphthocyclooctatetraene complexes: synthesis, characterization and catalytic activity in [5+2] cycloadditions. , 2012, Angewandte Chemie.

[7]  L. Takács,et al.  Temperature of the milling balls in shaker and planetary mills , 2006 .

[8]  James Mack,et al.  Conducting moisture sensitive reactions under mechanochemical conditions , 2012 .

[9]  James Mack,et al.  Mechanochemistry: opportunities for new and cleaner synthesis. , 2012, Chemical Society reviews.

[10]  I. Beletskaya,et al.  Non-conventional methodologies for transition-metal catalysed carbon–carbon coupling: a critical overview. Part 2: The Suzuki reaction , 2005 .

[11]  R. Blair,et al.  The scalability in the mechanochemical syntheses of edge functionalized graphene materials and biomass-derived chemicals. , 2014, Faraday discussions.

[12]  R. Willstätter,et al.  Über Cyclo‐octatetraen , 1911 .

[13]  Katharina Jacob,et al.  Scale-up of organic reactions in ball mills: process intensification with regard to energy efficiency and economy of scale. , 2014, Faraday discussions.

[14]  P. Wender,et al.  The synthesis of highly substituted cyclooctatetraene scaffolds by metal-catalyzed [2+2+2+2] cycloadditions: studies on regioselectivity, dynamic properties, and metal chelation. , 2009, Angewandte Chemie.

[15]  William C. Shearouse,et al.  Solvent-free Sonogashira coupling reaction via high speed ball milling , 2009 .

[16]  M. C. Lea.  On endothermic reactions effected by mechanical force , 1893, American Journal of Science.

[17]  James Mack,et al.  Scratching the catalytic surface of mechanochemistry: a multi-component CuAAC reaction using a copper reaction vial , 2013 .

[18]  L. Wondraczek,et al.  Influence of reaction parameters on the depolymerization of H2SO4-impregnated cellulose in planetary ball mills , 2016 .

[19]  C. Gollub,et al.  Mechanism of Reppe's nickel-catalyzed ethyne tetramerization to cyclooctatetraene: a DFT study. , 2004, Chemistry.

[20]  W. Reppe,et al.  Cyclisierende Polymerisation von Acetylen I Über Cyclooctatetraen , 1948 .

[21]  M. C. Lea.  On endothermic decompositions obstained by pressure; Part II, Transformations of energy by shearing stress , 1893, American Journal of Science.

[22]  James Mack,et al.  An inexpensive and recyclable silver-foil catalyst for the cyclopropanation of alkenes with diazoacetates under mechanochemical conditions. , 2015, Angewandte Chemie.

[23]  Arno Kwade,et al.  Experimental and Computational Investigation of Knoevenagel Condensation in Planetary Ball Mills , 2014 .

[24]  B. Ondruschka,et al.  Suzuki cross-couplings of (hetero)aryl chlorides in the solid-state , 2012 .

[25]  Z. Xi,et al.  Metal mediated synthesis of substituted cyclooctatetraenes. , 2007, Chemical communications.

[26]  James Mack,et al.  Comparison of shaking versus baking: further understanding the energetics of a mechanochemical reaction , 2014 .

[27]  J. Louie,et al.  [2+2+2] Cycloaddition Reactions Catalyzed by Transition Metal Complexes , 2006 .

[28]  Bernd Ondruschka,et al.  Fast copper-, ligand- and solvent-free Sonogashira coupling in a ball mill , 2010 .

[29]  L. Takács.  The historical development of mechanochemistry. , 2013, Chemical Society reviews.

[30]  B. Ondruschka,et al.  Mechanochemical solid-state Suzuki reactions using an in situ generated base. , 2008, ChemSusChem.

[31]  Guan-Wu Wang,et al.  Mechanochemical organic synthesis. , 2013, Chemical Society reviews.

[32]  Jean Martínez,et al.  Poly(ethylene glycol) as reaction medium for mild Mizoroki-Heck reaction in a ball-mill. , 2012, Chemical communications.

[33]  J. Krause,et al.  Efficient and regioselective nickel-catalyzed [2 + 2 + 2] cyclotrimerization of ynoates and related alkynes. , 2013, Organic & biomolecular chemistry.