Chemistry & Biochemistry

Chemistry Home

NMSU Home 

Arts & Sciences Home 

JAMES HERNDON, Ph.D.

B.S. Chemistry, University of North Carolina-Greensboro, 1979
M.S. Chemistry, Princeton University, Princeton, NJ, 1980
Ph.D. Chemistry, Princeton University, Princeton, NJ, 1983

 

Research in the Herndon group focuses on the discovery of new organotransition metal-based processes for use in organic synthesis. Of specific interest are reactions that transform simple starting materials into complex products in a general, predictable, efficient, and stereoselective manner. Most of our present activity involves exploration of the coupling reaction between Fischer carbene complexes and highly conjugated acetylene derivatives. Several useful processes have been identified from these studies, and two of the systems under study are detailed below.

The coupling of Fischer carbene complexes with enyne-aldehydes results in furan derivatives (eq 1). The unstable isobenzofuran ring system can be generated using benzo analogs (eq 2). Although unstable, this ring system very predictably undergoes Diels-Alder reactions. This reaction sequence serves as the cornerstone for preparation of pharmaceutically important structures (e.g. the estrogen-like structure depicted in eq 3) from two relatively simple components.

The coupling of Fischer carbene complexes with dienynes results in the synthesis of the benzofuran ring system (eq 4). This process has been found to be very and general and tolerant of a variety of substitution patterns. Numerous medicinally important compounds contain the benzofuran ring system and current research activity involves the synthesis of biologically active compounds for medicinal evaluation.

Recent Publications:

  • Herndon, J.W. "Annual Survey of the Carbon-Transition Metal Double and Triple Bond for the Year 2001" Coord. Chem. Rev. 2003, 227, Manuscript in Preparation.
  • Herndon, J.W. "Design of New Reaction Processes based on Cyclopropylcarbene Complexes." Current Organic Chemistry, In Press
  • Zhang, L.; Herndon, J.W. "Cross Metathesis Reactions using g,d-unsaturated Chromium Carbene Complexes." Tetrahedron Lett. 2002, 43, 4471-4473.
  • Ghorai, B.K.; Menon, S.; Johnson, D.L.; Herndon, J.W. "Inversion of the direction of stereoinduction in the coupling of chiral g,d-unsaturated Fischer carbene complexes with o-ethynylbenzaldehyde." Org. Lett. 2002, 4, 2121-2124.
  • Zhang, Y.; Herndon, J.W. "Synthesis of Furano[2,3-c]-pyran-3-one and Thieno[2,3-c]-pyran-3-one Derivatives through the Coupling of 3-Alkynyl-2-heteroaromatic Carboxaldehydes with Fischer Carbene Complexes; Total Synthesis of a Baccharis-derived Cadinene Derivative." J. Org. Chem. 2002, 67. 4177-4185.
  • Herndon, J.W. "Annual Survey of Carbon-Transition Metal Double and Triple Bond for the Year 2000" Coord. Chem. Rev. 2002, 227, 1-58.
  • Ghorai, B.K.; Herndon, J.W. "One-Step Convergent Synthesis of the Steroid Ring System via the Coupling of g,d-unsaturated Fischer Carbene Complexes with o-ethynylbenzaldehyde." Organic Letters 2001, 3, 3535-3538.
  • Herndon, J.W.; Zhang, Y.; Wang, K. "Palladium-catalyzed aminobenzannulation during Sonogashira couplings using o-bromoacetophenone." J. Organometal. Chem. 2001, 634, 1-4.
  • Zora, M.; Herndon, J.W.; Li, Y.; Rossi, J. "Ring Expansion in the Coupling of Fischer-Carbene Complexes with 1-Alkynyl-1-Hydroxy Cyclic Compounds." Tetrahedron 2001, 61, 5097-5107.
  • Jackson, T.J.; Herndon, J.W. "Annulation Selectivity in the Coupling of Fischer Carbene Complexes with o-Alkylbiphenyl and o-Alkynylstyrene Derivatives." Tetrahedron 2001, 61, 3859-3868.
  • Herndon, J.W. "Annual Survey of Carbon-Transition Metal Double and Triple Bond for the Year 1999" Coord. Chem. Rev. 2001, 214, 215-285.
  • Zhang, Y.; Herndon, J.W. "Synthesis of Furanopyrone and Thiophenopyrone Derivatives through the Coupling of 3-Alkynyl-2-heteroaromatic Carboxaldehydes with Fischer Carbene Complexes." Tetrahedron Lett. 2001, 42, 777-779.
  • Herndon, J.W.; Zhang, Y.; Wang, H.; Wang, K. "Synthesis of Benzofuran Derivatives through the Coupling of Conjugated Dienynes with Fischer Carbene Complexes." Tetrahedron Lett. 2000, 41, 8687-8690.
  • Jiang, D.; Herndon, J.W. "Generation and Trapping of Isobenzofuran Intermediates formed in the Coupling of Fischer Carbene Complexes and ortho-Alkynylbenzoyl Derivatives." Organic Letters 2000, 2, 1267-1269.
  • Herndon, J.W., Zhu, J.; Sampedro, D. "Synthesis of Alkylidenecyclopentenones and Dialkylidenecyclopentenones via the Coupling of Propargylic Alcohol and 2-Alkyne-1,4-diol Derivatives with Cyclopropylcarbene-Chromium Complexes." Tetrahedron 2000, 60, 4985-4993.
  • Zhang, Y., Herndon, J.W. "Selective Remote Functionalization of Alkyl Side Chains in the Coupling of Fischer Carbene Complexes with Conjugated Enediynes" Tetrahedron 2000, 60, 2175-2184.
  • Herndon, J.W. Book Review for: "Advances in Strained and Interesting Organic Molecules. Volume 8." J. Am. Chem. Soc. 2000, 122, 11570.
  • Herndon, J.W. Introduction to a Special Edition of Tetrahedron entitled: "Carbene Complexes in Organic Chemistry." Tetrahedon 2000, 60, R9-R9.
  • Herndon, J.W. "The Use of Fischer Carbene Complexes for the Preparation of Five-Membered Carbocyclic Rings." Tetrahedron 2000, 60, 1257-1280.
  • Herndon, J.W. "Annual Survey of Carbon-Transition Metal Double and Triple Bond for the Year 1998" Coord. Chem. Rev. 2000, 209, 387-451.
  • Herndon, J.W. "Applications of Carbene Complexes Directed Toward Organic Synthesis" Coord. Chem. Rev. 2000, 206-207, 237-262.

 
jherndon@nmsu.edu
Click here for MARC program web page
More information on Dr. Herndon and his research:.

 

Department of Chemistry and Biochemistry
New Mexico State University
PO Box 30001 -- MSC 3C
Las Cruces, NM 88003-8001
505-646-2505
505-646-2649 FAX