Research Interests:

  • Organic transformations
  • Microwave assisted synthesis
  • Mechanistic investigations
  • Bioorganometallics
  • Green chemistry

    Courses Taught:

  • Organic Chemistry
  • Organic Laboratory
  • Catalysis: Organic Transformations
  • Inorganic Chemistry
  • Advanced Inorganic Chemistry
  • Polymer Chemistry
  • General Chemistry
  • Research in the Sciences
Summer Research Group 2011

Recent Group News:

  • Fall 2013: Our work on developing an acid, silver, and solvent free method for the gold-catalyzed hydrophenoxylation of internal alkynes has been published. LINK Congrads Marci, Dan, Erica, Kevin, Rosa, Erin, Victoria, and Aakash! This invited contribution is part of a special issue of the Beilstein Journal of Organic Chemistry on Gold Chemistry edited by Dean Toste. Our paper was one of the top 10 most downloaded articles in October!
  • Fall 2013: Daniel, Erica, Kevin, and Rosa present their work on hydrophenoxylation chemistry at the Northeastern Regional ACS meeting!
  • Fall 2013: Professor Stockland has been promoted to Full Professor!
  • Spring 2013: Professor Stockland has been awarded a research grant from the NSF to develop a new class of metalated nucleosides!
  • Spring 2013: Undergraduates Erica Miller, Kevin Garcia, Victoria Resh, and Aakash Shah join the group!
  • Fall 2012: Heathers communication on microwave assisted synthesis of arylgold compounds was published in Dalton Transactions LINK. Nice work Heather!
  • Fall 2012: Professor Stockland gave a talk on strategies for incorporating multinuclear NMR spectroscopy in research and teaching at the fall ACS meeting.
  • Summer 2012: Heather successfully defended her MS thesis!
  • Summer 2012: Marci successfully defended her MS thesis!
  • Spring 2012: Professor Stockland was awarded a Petroleum Research Fund grant to develop a new class of metallopolymers.
  • Spring 2012: Professor Stockland was awarded the Scadden Fellowship. This award is presented to two faculty (annually) at Bucknell for meritorious research.
  • Fall 2011: Our work on phospha-Michael additions to internal alkenes has been published in the Journal of Organic Chemistry LINK. Congratulations Heather, Marci, Kyle, Anthony, Jason, Eric, Krysta, and Tim!
  • Fall 2011: Our P-H activation paper has been published in Dalton Transactions LINK. Congratulations Jerry, Mark, and Meghan! This paper has recently been selected as a "HOT Article."
  • Fall 2011: Jorge Alvarenga joins the group to work on peptide synthesis.
  • Summer 2011: Cameron McConnell joins the group to work on palladium catalyzed phosphonylation chemistry.
  • Summer 2011: Marci Richard is awarded the Gebhardt Fellowship
  • Summer 2011: Tim Bergeron successfully defends his thesis - nice workTim!
  • Spring 2011: Professor Sockland talks about P-H activation and hydrophosphinylation at the Spring ACS meeting in California.
  • Spring 2011: Cameron McConnell is awarded a Bucknell Undergraduate Research Fellowship for summer 2011
  • Spring 2011: Marci and Kyle's chemistry appears in J. Organomet. Chem. (2011, 696, 123). This invited article is part of a thematic issue on the catalytic addition of E-H bonds to non-activated carbon-carbon multiple bonds.
Older group news
  • Professor Stockland has been honored with the William Pierce Boger Jr. Award for Teaching Excellence in Natural Sciences! Read the Bucknell press release.
  • Jerry Manbeck's (BS, '06) chemistry with metallosteroids is published in J. Am. Chem. Soc.!
  • Professor Stockland's book chapter on Microwave Assisted Organic Synthesis appeared in Microwave Heating as a Tool for Sustainable Chemistry. Nicholas Leadbeater, ed. CRC Press, 2010
  • Professor Stockland's review from 2008 in Current Organic Chemistry has been identified as one of the most accessed/downloaded reviews from the last three years.

 

Selected Recent Results (undergraduate authors underlined)

Acid, silver, and solvent-free gold catalyzed hydrophenoxylation of internal alkynes. M. E. Richard, D. V. Fraccica, K. J. Garcia, E. J. Miller, R. M. Ciccarelli, E. C. Holahan, V. L. Resh, A. Shah, P. M. Findeis, and R. A. Stockland Jr. Beilstein J. Org. Chem. 2013, 9, 2002-2008. Invited contribution to a thematic series on gold catalysis edited by Dean Toste. Our paper was one of the top 10 most downloaded articles in October!

Rapid Synthesis of Arylgold Compounds Using Dielectric Heating. H.K. Lenker, T.G. Gray and R.A. Stockland Jr. Dalton Trans. 2012, 41, 13274-13276.

Phospha-Michael Additions to Activated Internal Alkenes: Steric and Electronic Effects. Lenker, H, K.; Richard, M. E.; Reese, K. P.; Carter, A. F.; Zawisky, J. D.; Winter, E. F.; Bergeron, T. W.; Guydon, K. S.; Stockland, R. A., Jr. J. Org. Chem. 2012,77, 1378-1385.

P-H activation using alkynylgold substrates: steric and electronic effects. Manbeck, G.F.; Kohler, M.C.; Porter, M.R.; Stockland, R.A.Jr. Dalton Trans. 2011, 40, 12595-12606. This paper has recently been selected as a "HOT Article."

Probing the Steric Limits of Rhodium Catalyzed Hydrophosphinylation.  E-H addition vs. Dimerization/Oligomerization/Polymerization, M.E. Richard, K. P Reese, J. J. Stone, P. D. Pickett, E. S. Tillman, R. A. Stockland Jr., J. Organomet. Chem. 2011, 696, 123.  Invited contribution for a special issue on catalytic addition of E-H bonds to non-activated carbon-carbon multiple bonds

Luminescent Au(I)/Cu(I) Alkynyl Clusters with an Ethynyl Steroid and Related Aliphatic Ligands: an Octanuclear Au4Cu4 Cluster and Luminescence Polymorphism in Au3Cu2 Clusters. Manbeck, G. F.; Brennessel, W.W.; Stockland, R. A. Jr.; Eisenberg, R.  J. Am Chem. Soc. 2010, 132, 12307.

Microwave Heating as a Tool for Clean Organic Synthesis.  Stockland, R.A. Jr. in Microwave Heating as a Tool for Sustainable Chemistry. Nicholas Leadbeater, ed. CRC Press, 2010

Arylpalladium Phosphonate Complexes as Reactive Intermediates in Phosphorus-Carbon Bond Forming Reactions, Mark C. Kohler, T. V. Grimes, X. Wang,  T. R. Cundari, and R. A. Stockland Jr. Organometallics 2009, 28, 1193.

Development of a Room Temperature Hirao Reaction, M.C.Kohler, J. G. Sokol, and R. A. Stockland Jr. Tetrahedron Lett. 2009, 50, 457.

Microwave Assisted Heterofunctionalization of Alkenes, D. Ide, M. Eastlund, C. Jupe, and R. A. Stockland Jr. Curr. Org. Chem. 2008, 12, 1258. (invited review)

Synthesis, Characterization, and Reactivity of a Hexane Soluble Silver Salt. R. A. Stockland Jr., B. D. Wilson, C. C. Goodman, B. J. Giese, and F. L. Shrimp III J. Chem. Ed. 2007, 84, 694.

Modern NMR Spectroscopy in Education, ACS symposium Series Volume 969, Eds. David S. Rovnyak and R. A. Stockland Jr., 2007.

Remarkable Tolerance of Ethynyl Steroids to Air and Water in Hydrophosphinylation Reactions: Reaction Scope and Limitations. R. A. Stockland Jr. A. J. Lipman, J. A. Bawiec, P. E. Morrison, I. A. Guzei, P. M. Findeis, J. F. Tamblin. J. Organomet. Chem. 2006, 691, 4042.

Steric and Electronic Effects on Arylphosphonate Elimination from Organopalladium Complexes. M. C. Kohler, R. A. Stockland Jr., and N. P. Rath Organometallics 2006, 25, 5746.

Organometallic Complexes Containing 17-Ethynyl-17 b -hydroxyandrost-4-en-3-one and Related Ethynyl Steroids. R. A. Stockland Jr., M. C. Kohler, I. A. Guzei, M. E. Kastner, and J. A. Bawiec, III, R. B. Hochberg, D. C. Labaree Organometallics, 2006, 25, 2475.

Microwave Assisted Regioselective Addition of P(O)-H Bonds to Alkenes Without Added Solvent or Catalyst. R. I. Taylor, L.E. Thompson, P.B. Patel, and R.A. Stockland Jr. Org. Lett. 2005, 7, 851.

Organosoluble Copper Clusters as Precatalysts for Carbon-Heteroelement Bond Forming Reactions: Microwave and Conventional Heating. G. F. Manbeck, A. J. Lipman, R. A. Stockland Jr., A. L. Freidl, A. F. Hasler, J. J. Stone, and I. A. Guzei J. Org. Chem. 2005, 70, 244.

Funding:

My students and I thank the National Science Foundation, the Camille and Henry Dreyfus Foundation, the Petroleum Research Fund, Bristol-Myers Squibb, Merck Research, and Pfizer for financial support of our work.