Facile preparation of various heteroaromatic compounds via azatitanacyclopentadiene intermediates.

  title={Facile preparation of various heteroaromatic compounds via azatitanacyclopentadiene intermediates.},
  author={Daisuke Suzuki and Youhei Nobe and Yuko Watai and Ryoichi Tanaka and Yuuki Takayama and Fumie Sato and Hirokazu Urabe},
  journal={Journal of the American Chemical Society},
  volume={127 20},
Coupling of acetylene, nitrile, and a titanium reagent, Ti(O-i-Pr)(4)/2 i-PrMgCl, generated new azatitanacyclopentadienes in a highly regioselective manner. Their subsequent reaction with sulfonylacetylene afforded pyridyltitanium compounds, which, upon reaction with electrophiles, gave substituted pyridines virtually as a single isomer. When optically active nitriles were used in this reaction, chiral pyridines were obtained without loss of the enantiopurity. Alternatively, the… 
24 Citations
Oxidative Aza-Annulation of Enynyl Azides to 2-Keto/Formyl-1H-pyrroles.
A method for the construction of pyrroles bearing a 2-keto or formyl group through the intramolecular oxidative aza-annulation of enynyl azides is reported for the first time. It involves a
Regioselective Pd-Catalyzed Synthesis of 2,3,6-Trisubstituted Pyridines from Isoxazolinones.
An operationally simple approach that makes use of readily accessible isoxazolinones and allows an effective, scalable and practical access to various previously unknown 2,3,6-trisubstituted pyridines.
Modular synthesis of multisubstituted furans through palladium-catalyzed three-component condensation of alkynylbenziodoxoles, carboxylic acids, and imines.
The Pd(OAc)2 -catalyzed room-temperature condensation reaction tolerates a broad range of functional groups in each of the reaction components, and enables highly modular and flexible synthesis of variously substituted furans.
MeOTf-Mediated Annulation of Alkylnitriles and Arylalkynes Leading to Polysubstituted NH-Pyrroles.
A metal-free multicomponent domino reaction for the highly regioselective synthesis of tetrasubstituted NH-pyrroles from readily available alkylnitriles, arylalkynes, and MeOTf has been developed. A
Reactions of Zirconocene Butadiyne or Monoyne Complexes with Nitriles: Straightfoward Synthesis of Functionalized Pyrimidines
Zirconium-mediated multicomponent reactions of silyl-butadiynes with two molecules of aryl nitriles are described, which provide rapid access to polysubstituted pyrimidines in a regioselective manner
Tandem Synthesis of Tetrasubstituted NH Pyrroles from Simple Nitriles.
An efficient tandem route to obtain tetrasubstituted N H pyrroles in a one-pot manner has been developed, staring from simple nitriles, ethyl bromoacetates, and zinc. This reaction involves oxidative
Approach to Trisubstituted 3-Aminopyrrole Derivatives by Yb(OTf)3-Catalyzed [4+1] Annulation of 2-Azadiene with Me3SiCN
In the present study, we found a novel approach to the simple and practical synthesis of 3-aminopyrrole derivatives through the four-component coupling reaction of a functionalized silane, a nitrile,
Cationic Rhodium(I)/Modified-BINAP Catalyzed [2+2+2] Cycloaddition of Alkynes with Nitriles
Cationic rhodium(I)/modified-BINAP complexes catalyze a chemo- and regioselective [2+2+2] cycloaddition of a wide variety of alkynes and nitriles leading to highly functionalized pyridines under mild