Selective ruthenium-catalyzed methylation of 2-arylethanols using methanol as C1 feedstock.

We describe the selective cross coupling of methanol and 2-arylethanols using a combination of Ru-MACHO (RuHCl(PNP(Ph))CO) and Shvo's diruthenium complex as catalysts. The desired domino transformation takes place via so-called borrowing hydrogen methodology, which constitutes an ideal example of green chemistry.

[1]  Yong Cao,et al.  Supported gold catalysis: from small molecule activation to green chemical synthesis. , 2014, Accounts of chemical research.

[2]  Y. Obora,et al.  Iridium-catalyzed selective α-methylation of ketones with methanol. , 2014, Chemical communications.

[3]  R. Ludwig,et al.  Base-free hydrogen generation from methanol using a bi-catalytic system. , 2014, Chemical communications.

[4]  Darren L. Poole,et al.  Rhodium-Catalyzed Ketone Methylation Using Methanol Under Mild Conditions: Formation of α-Branched Products** , 2013, Angewandte Chemie.

[5]  M. Beller,et al.  Selective hydrogen production from methanol with a defined iron pincer catalyst under mild conditions. , 2013, Angewandte Chemie.

[6]  Xiaoyuan Zou,et al.  Direct use of methanol as an alternative to formaldehyde for the synthesis of 3,3'-bisindolylmethanes (3,3'-BIMs). , 2013, Chemistry.

[7]  R. Franke,et al.  Ruthenium-catalyzed hydroformylation/reduction of olefins to alcohols: extending the scope to internal alkenes. , 2013, Journal of the American Chemical Society.

[8]  R. Rodríguez‐Lugo,et al.  A homogeneous transition metal complex for clean hydrogen production from methanol-water mixtures. , 2013, Nature chemistry.

[9]  F. Glorius,et al.  N-formylation of amines by methanol activation. , 2013, Organic letters.

[10]  M. Beller,et al.  Low-temperature aqueous-phase methanol dehydrogenation to hydrogen and carbon dioxide , 2013, Nature.

[11]  K. Dyballa,et al.  From olefins to alcohols: efficient and regioselective ruthenium-catalyzed domino hydroformylation/reduction sequence. , 2013, Angewandte Chemie.

[12]  E. V. Van der Eycken,et al.  Recent approaches for C-C bond formation via direct dehydrative coupling strategies. , 2013, Chemical Society reviews.

[13]  Feng Li,et al.  General and efficient method for direct N-monomethylation of aromatic primary amines with methanol , 2012 .

[14]  H. Alper,et al.  Synthesis of Alcohols via a Rhodium‐Catalyzed Hydroformylation– Reduction Sequence using Tertiary Bidentate Amine Ligands , 2012 .

[15]  H. Neumann,et al.  The Catalytic Amination of Alcohols , 2011 .

[16]  M. Beller,et al.  Efficient hydrogen production from alcohols under mild reaction conditions. , 2011, Angewandte Chemie.

[17]  A. Lough,et al.  Osmium and Ruthenium Catalysts for Dehydrogenation of Alcohols , 2011 .

[18]  Ryan A. Mesch,et al.  Iridium-catalysed direct C–C coupling of methanol and allenes , 2011, Nature Chemistry.

[19]  M. Yus,et al.  Hydrogen autotransfer in the N-alkylation of amines and related compounds using alcohols and amines as electrophiles. , 2010, Chemical reviews.

[20]  R. Crabtree,et al.  Dehydrogenation as a substrate-activating strategy in homogeneous transition-metal catalysis. , 2010, Chemical reviews.

[21]  T. Williams,et al.  Discovery, applications, and catalytic mechanisms of Shvo's catalyst. , 2010, Chemical reviews.

[22]  Xiaonian Li,et al.  One-pot synthesis of N,N-dimethylaniline from nitrobenzene and methanol , 2009 .

[23]  M. Whittlesey,et al.  Transition metal catalysed reactions of alcohols using borrowing hydrogen methodology. , 2009, Dalton transactions.

[24]  W. Hagmann,et al.  The many roles for fluorine in medicinal chemistry. , 2008, Journal of medicinal chemistry.

[25]  S. Purser,et al.  Fluorine in medicinal chemistry. , 2008, Chemical Society reviews.

[26]  Jonathan M. J. Williams,et al.  Borrowing hydrogen in the activation of alcohols , 2007 .

[27]  M. Yus,et al.  Alcohols as electrophiles in C--C bond-forming reactions: the hydrogen autotransfer process. , 2007, Angewandte Chemie.

[28]  O. Badr,et al.  Renewable hydrogen utilisation for the production of methanol , 2007 .

[29]  S. C. Roy,et al.  Synthesis of lower olefins from methanol and subsequent conversion of ethylene to higher olefins via oligomerisation , 2004 .

[30]  Wenzhu Lin,et al.  A study of ethanol dehydrogenation reaction in a palladium membrane reactor , 2004 .

[31]  Timothy R. Griffin,et al.  Promotion of iridium-catalyzed methanol carbonylation: mechanistic studies of the cativa process. , 2004, Journal of the American Chemical Society.

[32]  G. Verardo,et al.  Cyclopentadienyl RuII Complexes as Highly Efficient Catalysts for the N‐Methylation of Alkylamines by Methanol , 2004 .

[33]  A. R. Galletti,et al.  Selective synthesis of isobutanol by means of the Guerbet reaction: Part 3: Methanol/n-propanol condensation by using bifunctional catalytic systems based on nickel, rhodium and ruthenium species with basic components , 2003 .

[34]  M. Girolamo,et al.  Synthesis of isobutanol by the Guerbet condensation of methanol with n-propanol in the presence of heterogeneous and homogeneous palladium-based catalytic systems , 2003 .

[35]  G. Süss-Fink,et al.  Ligand effects in the rhodium-catalyzed carbonylation of methanol , 2003 .

[36]  M. Girolamo,et al.  Selective synthesis of isobutanol by means of the Guerbet reaction: Part 2: Reaction of methanol/ethanol and methanol/ethanol/n-propanol mixtures over copper based/MeONa catalytic systems , 2003 .

[37]  M. Girolamo,et al.  Selective synthesis of isobutanol by means of the Guerbet reaction - Part 1. Methanol/n-propanol condensation by using copper based catalytic systems , 2003 .

[38]  Weiguo Song,et al.  The mechanism of methanol to hydrocarbon catalysis. , 2003, Accounts of chemical research.

[39]  Marcel Liauw,et al.  Formaldehyde synthesis from methanol over silver catalysts , 2003 .

[40]  W. Szeja,et al.  Cleavage of 2-phenyl-1,3-dioxolanes and benzyl ethers by catalytic transfer hydrogenation , 1986 .

[41]  S. Hanessian,et al.  Facile Cleavage of Benzyl Ethers by Catalytic Transfer Hydrogenation , 1981 .

[42]  T. Cole,et al.  Reductions with carbon monoxide and water in place of hydrogen. 1. Hydroformylation reaction and water gas shift reaction , 1977 .

[43]  Y. Obora,et al.  Conferences and Meetings , 1966, British medical journal.