Iridium-catalyzed methylation of indoles and pyrroles using methanol as feedstock

Iridium-catalyzed methylation of indoles and pyrroles using methanol as the methylating agent was achieved. This transformation takes place via a borrowing hydrogen methodology under an air atmosphere, which constitutes a direct route to 3-methyl-indoles and methyl-pyrroles.

[1]  A. Seayad,et al.  Efficient Ruthenium-Catalyzed N-Methylation of Amines Using Methanol , 2015 .

[2]  G. Piersanti,et al.  Iridium-catalyzed direct synthesis of tryptamine derivatives from indoles: exploiting n-protected β-amino alcohols as alkylating agents. , 2015, The Journal of organic chemistry.

[3]  P. Andersson,et al.  C-C coupling of ketones with methanol catalyzed by a N-heterocyclic carbene-phosphine iridium complex. , 2015, Chemistry.

[4]  Darren L. Poole,et al.  Hydrogen-Borrowing and Interrupted-Hydrogen-Borrowing Reactions of Ketones and Methanol Catalyzed by Iridium** , 2014, Angewandte Chemie.

[5]  M. Beller,et al.  Selective ruthenium-catalyzed methylation of 2-arylethanols using methanol as C1 feedstock. , 2014, Chemical communications.

[6]  Y. Obora Recent Advances in α-Alkylation Reactions using Alcohols with Hydrogen Borrowing Methodologies , 2014 .

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

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

[9]  S. H. Siddiki,et al.  General and selective C-3 alkylation of indoles with primary alcohols by a reusable Pt nanocluster catalyst. , 2013, Chemistry.

[10]  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.

[11]  Y. Oe,et al.  Transition‐Metal‐Catalyzed Regioselective Alkylation of Indoles with Alcohols , 2013 .

[12]  M. Hara,et al.  Selective aerobic oxidation of methanol in the coexistence of amines by nanoporous gold catalysts: highly efficient synthesis of formamides. , 2013, Chemistry.

[13]  M. Yus,et al.  Environmentally friendly and regioselective C3-alkylation of indoles with alcohols through a hydrogen autotransfer strategy , 2013 .

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

[15]  S. Pan,et al.  Recent Advances in Iridium-Catalyzed Alkylation of C–H and N–H Bonds , 2013 .

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

[17]  A. M. Chibiryaev,et al.  Tetramethyl orthosilicate as a sharp-selective catalyst of C3-methylation of indole by supercritical methanol , 2012 .

[18]  A. C. Marr Organometallic hydrogen transfer and dehydrogenation catalysts for the conversion of bio-renewable alcohols , 2012 .

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

[20]  P. Elsinghorst,et al.  Synthesis of deuterium‐labeled d3‐androstenone and d3‐skatole for boar taint analysis , 2011 .

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

[22]  T. Matsuda,et al.  Ring-methylation of pyrrole and indole using supercritical methanol , 2010 .

[23]  M. Beller,et al.  Selective ruthenium-catalyzed N-alkylation of indoles by using alcohols. , 2010, Chemistry.

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

[25]  R. Grigg,et al.  [Cp*IrCl2]2-catalyzed indirect functionalization of alcohols: novel strategies for the synthesis of substituted indoles. , 2007, Organic letters.

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

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

[30]  K. Tani,et al.  Efficient transfer hydrogenation of alkynes and alkenes with methanol catalysed by hydrido(methoxo)iridium(III) complexes , 1999 .

[31]  G. Yost,et al.  Mechanistic studies on the cytochrome P450-catalyzed dehydrogenation of 3-methylindole. , 1996, Chemical research in toxicology.

[32]  R. Grigg,et al.  Oxidation of alcohols by transition metal complexes part V. Selective catalytic monoalkylation of arylacetonitriles by alcohols , 1981 .

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