Iron‐Catalysed Borylation of Arenediazonium Salts to Give Access to Arylboron Derivatives via Aryl(amino)boranes at Room Temperature

Complementary to previously described Miyaura borylation methods, a new access to boron derivatives via aryl(amino)boranes is described. Direct coupling between aryldiazonium salts and diisopropylaminoborane is catalysed by 0.1% ferrocene leading to the formation of a carbon-boron bond. The obtained aryl(amino)boranes could eventually then be transformed into boronic acids, boronates or borates.

[1]  Jian Yu,et al.  Metal‐Free, Visible Light‐Induced Borylation of Aryldiazonium Salts: A Simple and Green Synthetic Route to Arylboronates , 2012 .

[2]  S. Buchwald,et al.  Continuous-flow synthesis of monoarylated acetaldehydes using aryldiazonium salts. , 2012, Journal of the American Chemical Society.

[3]  P. Chirik,et al.  Iron Catalysts for Selective Anti-Markovnikov Alkene Hydrosilylation Using Tertiary Silanes , 2012, Science.

[4]  T. Hatakeyama,et al.  Cross-coupling of non-activated chloroalkanes with aryl Grignard reagents in the presence of iron/N-heterocyclic carbene catalysts. , 2012, Organic letters.

[5]  E. Nakamura,et al.  Iron-catalyzed regio- and stereoselective chlorosulfonylation of terminal alkynes with aromatic sulfonyl chlorides. , 2012, Organic letters.

[6]  Shauna M. Paradine,et al.  Iron-catalyzed intramolecular allylic C-H amination. , 2012, Journal of the American Chemical Society.

[7]  M. Vaultier,et al.  Aminoborylation/Suzuki-Miyaura tandem cross coupling of aryl iodides as efficient and selective synthesis of unsymmetrical biaryls. , 2012, Chemical communications.

[8]  I. Manners,et al.  Photoactivated, iron-catalyzed dehydrocoupling of amine-borane adducts: formation of boron-nitrogen oligomers and polymers. , 2011, Chemistry.

[9]  Songlin Zhang,et al.  Efficient Iron/Copper-CocatalyzedO-Arylation of Phenols with Bromoarenes , 2011 .

[10]  T. Ritter,et al.  A strategy for the synthesis of well-defined iron catalysts and application to regioselective diene hydrosilylation. , 2010, Journal of the American Chemical Society.

[11]  I. Manners,et al.  Amine- and phosphine-borane adducts: new interest in old molecules. , 2010, Chemical reviews.

[12]  Anne Staubitz,et al.  Ammonia-borane and related compounds as dihydrogen sources. , 2010, Chemical reviews.

[13]  T. Hatanaka,et al.  C-H bond activation/borylation of furans and thiophenes catalyzed by a half-sandwich iron N-heterocyclic carbene complex. , 2010, Chemistry, an Asian journal.

[14]  J. Wang,et al.  Direct conversion of arylamines to pinacol boronates: a metal-free borylation process. , 2010, Angewandte Chemie.

[15]  Chang-Liang Sun,et al.  Cross-coupling of alkenyl/aryl carboxylates with Grignard reagent via Fe-catalyzed C-O bond activation. , 2009, Journal of the American Chemical Society.

[16]  T. Hatakeyama,et al.  Iron-catalyzed Negishi coupling toward an effective olefin synthesis. , 2009, Organic letters.

[17]  T. Hatakeyama,et al.  Highly selective biaryl cross-coupling reactions between aryl halides and aryl Grignard reagents: a new catalyst combination of N-heterocyclic carbenes and iron, cobalt, and nickel fluorides. , 2009, Journal of the American Chemical Society.

[18]  J. Cvengroš,et al.  Coming of age: sustainable iron-catalyzed cross-coupling reactions. , 2009, ChemSusChem.

[19]  B. Singaram,et al.  Reductions of aliphatic and aromatic nitriles to primary amines with diisopropylaminoborane. , 2009, The Journal of organic chemistry.

[20]  T. Hatakeyama,et al.  Iron-catalyzed enyne cross-coupling reaction. , 2008, Organic letters.

[21]  M. Beller,et al.  Iron‐Catalyzed Aromatic Substitutions , 2008 .

[22]  C. Bolm,et al.  Iron-catalyzed intramolecular o-arylation: synthesis of 2-aryl benzoxazoles. , 2008, Organic letters.

[23]  C. Bolm,et al.  Iron-catalysed carbon-heteroatom and heteroatom-heteroatom bond forming processes. , 2008, Chemical Society reviews.

[24]  C. Bolm,et al.  Iron-catalyzed C-O cross-couplings of phenols with aryl iodides. , 2008, Angewandte Chemie.

[25]  C. Bolm,et al.  Iron-catalyzed N-arylation of nitrogen nucleophiles. , 2007, Angewandte Chemie.

[26]  J. Hartwig,et al.  Meta halogenation of 1,3-disubstituted arenes via iridium-catalyzed arene borylation. , 2007, Journal of the American Chemical Society.

[27]  Carsten Bolm Prof.,et al.  Iron-Catalyzed N-Arylation of Nitrogen Nucleophiles† , 2007 .

[28]  J. Cossy,et al.  Iron-catalyzed cross-coupling of alkyl halides with alkenyl grignard reagents. , 2007, Angewandte Chemie.

[29]  T. Hatakeyama,et al.  Iron-catalyzed selective biaryl coupling: remarkable suppression of homocoupling by the fluoride anion. , 2007, Journal of the American Chemical Society.

[30]  C. Chai,et al.  Iron-Catalysed sp3–sp3 Cross-Coupling Reactions of Unactivated Alkyl Halides with Alkyl Grignard Reagents , 2007 .

[31]  J. Hartwig,et al.  One-pot synthesis of arylboronic acids and aryl trifluoroborates by Ir-catalyzed borylation of arenes. , 2007, Organic letters.

[32]  M. Taillefer,et al.  Efficient iron/copper co-catalyzed arylation of nitrogen nucleophiles. , 2007, Angewandte Chemie.

[33]  D. Bruce,et al.  Iron-phosphine, -phosphite, -arsine, and -carbene catalysts for the coupling of primary and secondary alkyl halides with aryl Grignard reagents. , 2006, The Journal of organic chemistry.

[34]  N. Miyaura,et al.  Mechanism of the mild functionalization of arenes by diboron reagents catalyzed by iridium complexes. Intermediacy and chemistry of bipyridine-ligated iridium trisboryl complexes. , 2005, Journal of the American Chemical Society.

[35]  M. Vaultier,et al.  Stereospecific palladium-catalyzed borylation reaction of 1-alkenyl halides with diispropylaminoborane , 2005 .

[36]  A. Fürstner,et al.  Advances in Iron Catalyzed Cross Coupling Reactions , 2005 .

[37]  C. E. Webster,et al.  Rhodium boryl complexes in the catalytic, terminal functionalization of alkanes. , 2005, Journal of the American Chemical Society.

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

[39]  M. Vaultier,et al.  Monomeric (dialkylamino)boranes: a new and efficient boron source in palladium catalyzed C-B bond formation with aryl halides. , 2003, Chemical communications.

[40]  N. Miyaura,et al.  Synthesis of pinacol arylboronates via cross-coupling reaction of bis(pinacolato)diboron with chloroarenes catalyzed by palladium(0)–tricyclohexylphosphine complexes , 2001 .

[41]  N. Miyaura,et al.  Chemistry of Group 13 element-transition metal linkage — the platinum- and palladium-catalyzed reactions of (alkoxo)diborons , 2000 .

[42]  N. Miyaura,et al.  Synthesis of arylboronates via the palladium(0)-catalyzed cross-coupling reaction of tetra(alkoxo)diborons with aryl triflates , 1997 .

[43]  P. Knochel,et al.  Neue Cobalt‐ und Eisen‐katalysierte Reaktionen mit Organozinkverbindungen , 1996 .

[44]  P. Knochel,et al.  New Cobalt‐ and Iron‐Catalyzed Reactions of Organozinc compounds , 1996 .

[45]  N. Miyaura,et al.  Palladium(0)-Catalyzed Cross-Coupling Reaction of Alkoxydiboron with Haloarenes: A Direct Procedure for Arylboronic Esters , 1995 .

[46]  Xiaoming He,et al.  Hydrocarbon Functionalization by Transition Metal Boryls , 1995 .

[47]  K. Johnson,et al.  Homolytic reactions of ligated boranes. Part 13. An electron spin resonance study of radical addition to aminoboranes , 1989 .

[48]  G. Molander,et al.  Iron catalyzed cross-coupling reactions. Synthesis of arylethenes. , 1983 .

[49]  J. Kochi,et al.  Vinylation of Grignard reagents. Catalysis by iron , 1971 .

[50]  A. Beckwith,et al.  The reaction of ferricinium ion with phenylazotriphenylmethane , 1966 .

[51]  G. Broadhead,et al.  Ferrocene derivatives. Part II. Arylation , 1955 .