Palladium-catalyzed regioselective allylation of five-membered heteroarenes with allyltributylstannane.

Palladium-catalyzed allylation reactions of 2-(chloromethyl)thiophenes, 2-(chloromethyl)furans, and N-protected 2-(chloromethyl)-1H-pyrroles with allyltributylstannane were described in this study. This type of allylation reaction regioselectively occurred on the heteroarene rings to produce allylated dearomatization products or allylated heteroarenes with satisfactory yields.

[1]  D. Procter,et al.  Nucleophilic ortho-Allylation of Pyrroles and Pyrazoles: An Accelerated Pummerer/Thio-Claisen Rearrangement Sequence , 2013, Organic letters.

[2]  F. Glorius,et al.  Mild rhodium(III)-catalyzed direct C-H allylation of arenes with allyl carbonates. , 2013, Angewandte Chemie.

[3]  V. Rawal,et al.  Palladium-catalyzed decarboxylative allylation and benzylation of N-alloc and N-Cbz indoles. , 2013, Organic letters.

[4]  R. Batey,et al.  Regio- and stereoselective allylation and crotylation of indoles at C2 through the use of potassium organotrifluoroborate salts. , 2013, Angewandte Chemie.

[5]  S. You,et al.  Diversity oriented synthesis of indole-based peri-annulated compounds via allylic alkylation reactions , 2013 .

[6]  S. You,et al.  Asymmetric N-allylation of indoles through the iridium-catalyzed allylic alkylation/oxidation of indolines. , 2012, Angewandte Chemie.

[7]  B. Feringa,et al.  Highly enantioselective synthesis of 3-substituted γ-butenolides by palladium-catalyzed kinetic resolution of unsymmetrical allyl acetates. , 2012, Angewandte Chemie.

[8]  Baomin Wang,et al.  Friedel-Crafts-type allylation of nitrogen-containing aromatic compounds with allylic alcohols catalyzed by a [Mo3S4Pd(η3-allyl)] cluster. , 2012, The Journal of organic chemistry.

[9]  Fu‐She Han,et al.  PdCl2-catalyzed efficient allylation and benzylation of heteroarenes under ligand, base/acid, and additive-free conditions. , 2011, Chemical communications.

[10]  K. Hirano,et al.  Stereospecific copper-catalyzed C-H allylation of electron-deficient arenes with allyl phosphates. , 2011, Angewandte Chemie.

[11]  M. Niggemann,et al.  Calcium-catalyzed Friedel-Crafts alkylation at room temperature. , 2010, Angewandte Chemie.

[12]  O. Krokhin,et al.  Organocatalyzed Friedel–Crafts arylation of benzylic alcohols , 2010 .

[13]  Basker Sundararaju,et al.  Ruthenium(IV) complexes featuring P,O-chelating ligands: regioselective substitution directly from allylic alcohols. , 2010, Angewandte Chemie.

[14]  M. Wörle,et al.  Fast and highly regioselective allylation of indole and pyrrole compounds by allyl alcohols using Ru-sulfonate catalysts. , 2008, Journal of the American Chemical Society.

[15]  V. Rawal,et al.  Palladium-catalyzed beta-allylation of 2,3-disubstituted indoles. , 2008, Organic letters.

[16]  Weidong Rao,et al.  Gold-catalysed allylic alkylation of aromatic and heteroaromatic compounds with allylic alcohols. , 2008, Organic & biomolecular chemistry.

[17]  Dong Wang,et al.  Calix[n]arene sulfonic acids bearing pendant aliphatic chains as recyclable surfactant-type Brønsted acid catalysts for allylic alkylation with allyl alcohols in water , 2008 .

[18]  Ken Motokura,et al.  Nucleophilic substitution reactions of alcohols with use of montmorillonite catalysts as solid Brønsted acids. , 2007, The Journal of organic chemistry.

[19]  Zhenyang Lin,et al.  DFT studies on the mechanism of allylative dearomatization catalyzed by palladium. , 2006, Journal of the American Chemical Society.

[20]  B. Trost,et al.  Palladium-catalyzed enantioselective C-3 allylation of 3-substituted-1H-indoles using trialkylboranes. , 2006, Journal of the American Chemical Society.

[21]  G. Fabrizi,et al.  Synthesis and functionalization of indoles through palladium-catalyzed reactions. , 2005, Chemical reviews.

[22]  Y. Nishibayashi,et al.  Ruthenium-Catalyzed Allylation of Aromatic Compounds and Allylic Ether Formation , 2004 .

[23]  M. Bao,et al.  Facile allylative dearomatization catalyzed by palladium. , 2001, Journal of the American Chemical Society.