Iron-catalyzed N-alkylation using π-activated ethers as electrophiles.

A new method for the synthesis of diverse N-alkylation compounds was developed via an iron-catalyzed etheric C(sp(3))-O cleavage with the C-N bond formation in the reaction of π-activated ethers with various nitrogen-based nucleophiles. In addition, the mechanism of this reaction was investigated.

[1]  P. Ghorai,et al.  Direct substitution of hydroxy group of π-activated alcohols with electron-deficient amines using Re2O7 catalyst. , 2012, The Journal of organic chemistry.

[2]  Soon Hyeok Hong,et al.  Selective catalytic sp3 C-O bond cleavage with C-N bond formation in 3-alkoxy-1-propanols. , 2012, Organic letters.

[3]  Y. Miyamoto,et al.  Direct substitution of the hydroxy group with highly functionalized nitrogen nucleophiles catalyzed by Au(III). , 2011, Chemical communications.

[4]  Zhiping Li,et al.  Iron-catalyzed carbonylation-peroxidation of alkenes with aldehydes and hydroperoxides. , 2011, Journal of the American Chemical Society.

[5]  Guangbin Dong,et al.  Novel synthetic method for allylic amination of cyclic allylic ethers using chlorosulfonyl isocyanate , 2011 .

[6]  M. Shi,et al.  Chiral Bifunctional Thiourea–Phosphane Organocatalysts in Asymmetric Allylic Amination of Morita–Baylis–Hillman Acetates , 2011 .

[7]  V. Percec,et al.  Nickel-catalyzed cross-couplings involving carbon-oxygen bonds. , 2011, Chemical reviews.

[8]  Chang-Liang Sun,et al.  Direct C-H transformation via iron catalysis. , 2011, Chemical reviews.

[9]  M. Niggemann,et al.  Calcium‐Catalyzed Direct Amination of π‐Activated Alcohols , 2011 .

[10]  Da‐Gang Yu,et al.  Activation of "inert" alkenyl/aryl C-O bond and its application in cross-coupling reactions. , 2011, Chemistry.

[11]  Joshua D. Waetzig,et al.  Stereospecific nickel-catalyzed cross-coupling reactions of alkyl ethers: enantioselective synthesis of diarylethanes. , 2011, Journal of the American Chemical Society.

[12]  Youquan Deng,et al.  Organic ligand-free alkylation of amines, carboxamides, sulfonamides, and ketones by using alcohols catalyzed by heterogeneous Ag/Mo oxides. , 2011, Chemistry.

[13]  U. Schneider,et al.  Indium(I)-catalyzed alkyl-allyl coupling between ethers and an allylborane. , 2011, Chemical communications.

[14]  H. Imagawa,et al.  Hg(OTf)2-BINAPHANE-catalyzed enantioselective anilino sulfonamide allyl alcohol cyclization. , 2010, Chemistry.

[15]  Da‐Gang Yu,et al.  Exploration of new C-O electrophiles in cross-coupling reactions. , 2010, Accounts of chemical research.

[16]  G. Molander,et al.  Nickel-catalyzed C-O activation of phenol derivatives with potassium heteroaryltrifluoroborates. , 2010, Organic letters.

[17]  Lee M. Bishop,et al.  Catalytic C-O bond cleavage of 2-aryloxy-1-arylethanols and its application to the depolymerization of lignin-related polymers. , 2010, Journal of the American Chemical Society.

[18]  Nan Li,et al.  Catalytic regioselective synthesis of structurally diverse indene derivatives from N-benzylic sulfonamides and disubstituted alkynes. , 2010, Organic letters.

[19]  J. Klett,et al.  Cleave and capture chemistry illustrated through bimetallic-induced fragmentation of tetrahydrofuran. , 2010, Nature chemistry.

[20]  Su-Young Son,et al.  Non-oxidative vanadium-catalyzed C-O bond cleavage: application to degradation of lignin model compounds. , 2010, Angewandte Chemie.

[21]  Jimmy Wu,et al.  Mild two-step process for the transition-metal-free synthesis of carbon-carbon bonds from allylic alcohols/ethers and grignard reagents. , 2010, Journal of the American Chemical Society.

[22]  J. Oh,et al.  A Facile Synthesis of Lentiginosine Analogues Based on a Highly Regio‐ and Diastereoselective Allylic Amination Using Chlorosulfonyl Isocyanate , 2010 .

[23]  Y. Tu,et al.  Iron-catalyzed C(sp3)-C(sp3) bond formation through C(sp3)-H functionalization: a cross-coupling reaction of alcohols with alkenes. , 2009, Angewandte Chemie.

[24]  S. Pan,et al.  One-pot synthesis of symmetric and unsymmetric 1,1-bis-indolylmethanes via tandem iron-catalyzed C-H bond oxidation and C-O bond cleavage. , 2009, The Journal of organic chemistry.

[25]  N. Findlay,et al.  Metal-free reductive cleavage of C-O sigma-bonds in acyloin derivatives by an organic neutral super-electron-donor. , 2009, The Journal of organic chemistry.

[26]  Ch. Raji Reddy,et al.  Acid-catalyzed N-alkylation of tosylhydrazones using benzylic alcohols , 2009 .

[27]  N. Chatani,et al.  Nickel-catalyzed cross-coupling reaction of alkenyl methyl ethers with aryl boronic esters. , 2009, Organic letters.

[28]  C. Bolm,et al.  Copper-catalyzed cross-couplings with part-per-million catalyst loadings. , 2009, Angewandte Chemie.

[29]  R. Fan,et al.  Transition-metal-free intermolecular amination of sp3 C-H bonds with sulfonamides. , 2009, Organic letters.

[30]  M. Beller,et al.  Green and efficient synthesis of sulfonamides catalyzed by nano-Ru/Fe(3)O(4). , 2009, Journal of the American Chemical Society.

[31]  H. Amii,et al.  Selective aromatic carbon–oxygen bond cleavage of trifluoromethoxyarenes: a trifluoromethoxy group as a convertible directing group , 2008 .

[32]  Xue‐Liang Wu,et al.  Phosphotungstic Acid Catalyzed Amidation of Alcohols , 2008 .

[33]  T. Müller,et al.  Hydroamination: direct addition of amines to alkenes and alkynes. , 2008, Chemical reviews.

[34]  Zhangjie Shi,et al.  Benzylation of arenes through FeCl3-catalyzed Friedel–Crafts reaction via C–O activation of benzyl ether , 2008 .

[35]  T. Bach,et al.  Gold(III) Chloride‐Catalyzed Diastereoselective Alkylation Reactions with Chiral Benzylic Acetates , 2008 .

[36]  D. Powell,et al.  Copper triflate/t-BuOOAc-catalyzed amidation of allylic and benzylic acetates with sulfonamides , 2008 .

[37]  Yuyang Jiang,et al.  Efficient intermolecular iron-catalyzed amidation of C-H bonds in the presence of N-bromosuccinimide. , 2008, Organic letters.

[38]  Tao Wu,et al.  Methylation of arenes via Ni-catalyzed aryl C-O/F activation. , 2008, Chemical communications.

[39]  Zhangjie Shi,et al.  Direct benzylic alkylation via Ni-catalyzed selective benzylic sp3 C-O activation. , 2008, Journal of the American Chemical Society.

[40]  U. Jana,et al.  An efficient FeCl3-catalyzed amidation reaction of secondary benzylic and allylic alcohols with carboxamides or p-toluenesulfonamide , 2008 .

[41]  S. Marque,et al.  Intermolecular FeCl3‐Catalyzed Hydroamination of Styrenes , 2007 .

[42]  N. Chatani,et al.  Direct observation of the oxidative addition of the aryl carbon-oxygen bond to a ruthenium complex and consideration of the relative reactivity between aryl carbon-oxygen and aryl carbon-hydrogen bonds. , 2006, Journal of the American Chemical Society.

[43]  D. Powell,et al.  Copper-catalyzed amidation of allylic and benzylic C-H bonds. , 2006, Organic letters.

[44]  Y. Tu,et al.  A general approach to crinine-type Amaryllidaceae alkaloids : total syntheses of (±)-haemanthidine, (±)-pretazettine, (±)-tazettine, and (±)-crinamine , 2006 .

[45]  O. Zee,et al.  A concise synthesis of (−)-cytoxazone and (−)-4-epi-cytoxazone using chlorosulfonyl isocyanate , 2006 .

[46]  Y. Tu,et al.  General and efficient strategy for erythrinan and homoerythrinan alkaloids: syntheses of (+/-)-3-demethoxyerythratidinone and (+/-)-erysotramidine. , 2006, Organic letters.

[47]  O. Zee,et al.  Regioselective and diastereoselective amination with use of chlorosulfonyl isocyanate: a short and efficient synthesis of (-)-cytoxazone. , 2005, Organic letters.

[48]  L. Zani,et al.  Iron-catalyzed reactions in organic synthesis. , 2004, Chemical reviews.

[49]  J. Dankwardt.  Nickel-catalyzed cross-coupling of aryl grignard reagents with aromatic alkyl ethers: an efficient synthesis of unsymmetrical biaryls. , 2004, Angewandte Chemie.

[50]  H. Tajima,et al.  Secondary benzylation using benzyl alcohols catalyzed by lanthanoid, scandium, and hafnium triflate. , 2003, The Journal of organic chemistry.

[51]  B. Trost,et al.  Asymmetric transition-metal-catalyzed allylic alkylations: applications in total synthesis. , 2003, Chemical reviews.

[52]  G. C. Fu,et al.  Suzuki cross-couplings of alkyl tosylates that possess beta hydrogen atoms: synthetic and mechanistic studies. , 2002, Angewandte Chemie.

[53]  D. Laurenti,et al.  Palladium-tetraphosphine catalysed allylic substitution in water , 2001 .

[54]  M. Johannsen,et al.  Iron-catalyzed allylic amination , 1994 .

[55]  J. A. Donnelly,et al.  The chemistry of 2'-amino analogs of 2'-hydroxychalcone and its derivatives , 1990 .

[56]  H. Mayr,et al.  Competing [2 + 3] and [4 + 3] cycloadditions of C,N-diphenylnitrone with 1,3-dienes. Evidence for thermally nonequilibrated intermediates , 1989 .

[57]  L. Jurd.  Synthesis of Mannich bases of bioactive benzylphenols , 1984 .

[58]  Y. Okamoto,et al.  Chlorotrimethylsilane/Sodium Iodide/Zinc as a Simple and Convenient Reducing System; One-Pot Deoxygenation of Alcohols and Ethers , 1981 .