Research Areas

Synthesis of organic compounds

(selected results)

Our work on stereospecific phosphonate transfer from Au to Pd as well as development of a base-free synthesis of arylated nucleosides was published; Eur. J. Org. Chem. 2018, 2167.

This chemistry was selected for the journal cover!

Practical Functional Group Synthesis addresses the chemists working in these fields by offering a practical guide to modern functional group synthesis through carbon–heteroelement bondforming reactions. Each chapter focuses on a single type of heteroelement, with sub-sections discussing specific functional groups.

• A focus on operational simplicity, sustainability and microwave-assisted reactions

• Key and recent developments – which are otherwise scattered across journal literature – into a single source

• Over 100 detailed procedures for the preparation of carbon–heteroelement bonds

• A total of 25 troubleshooting guides with suggestions and approaches to address common challenges

• 7 chapters, 691 pages, Wiley, 2016

Convenient Access to Arylated Spirocyclic Bisphosphonates. T. M. Lord, S. L Casino, S. E. Hartzell, K. J. Garcia, R. D. Pike, R. A. Stockland Jr. ChemistrySelect, 2016, 1, 2188-2191. Highlighted in CHEMINFORM, 2016, 49, 134.

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, 2002-2009 Invited contribution to a thematic series on gold catalysis edited by Dean Toste.

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

Probing the Steric Limits of Rhodium Catalyzed Hydrophosphinylation. P-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, 123-129. Invited contribution for a special issue on catalytic addition of E-H bonds to non-activated carbon-carbon multiple bonds

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

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

Microwave Assisted Heterofunctionalization of Alkenes, D. M. Ide, M. P. Eastlund, C. L. Jupe, and R. A. Stockland Jr. Curr. Org. Chem. 2008, 12, 1258. (one of the most accessed reviews from 2008-2010).

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

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, 244-250.

Highlighted on www.organic-chemistry.org as a rare example of a successful Ullmann-type coupling reaction involving a tetrahydrofurfuryl alcohol

Microwave Assisted Regioselective Addition of P(O)-H Bonds to Alkenes Without Added Solvent or Catalyst. R. A. Stockland Jr., R. I. Taylor, L. E. Thompson, and P. Patel Org. Lett. 2005, 7, 851-853.

Inorganic/organometallic synthesis and mechanistic investigations

(selected results)

Our work on the synthesis and host-guest chemistry of diphosphite supported metallomacrocycles was published in Inorg. Chem. 2018, 57, 11662.

Molecular structure of the 32-membered metallomcrocycle as determined by X-ray. In the solid state, the collapsed form is held together by non-covalent (aurophilic) interactions

Resolved P-Metallated Nucleoside Phosphoramidites. E. J. Miller, K. J. Garcia, E. C. Holahan, R. M. Ciccarelli, R. A. Bergin, S. L. Casino, T. L. Bogaczyk, M. R. Krout, P. M. Findeis, and R. A. Stockland Jr. Inorg. Chem. 2014, 53, 12680-12682.

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

P-H activation using alkynylgold substrates: steric and electronic effects. G.F. Manbeck, M.C. Kohler, M.R. Porter, and R.A. Stockland Jr. Dalton Transactions 2011, 40, 12595-12606.

This paper was selected as a 2011 "HOT Article" by Dalton Transactions.

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.

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

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

Reductive Elimination from Metal Phosphonate Complexes: Circumvention of Competing Protonolysis Reactions. R. A. Stockland Jr., A. M. Levine, M. T. Giovine; I. A. Guzei, and J. C. Cannistra Organometallics 2004, 23, 647-656.

Coupling of Aryl Halides with Aryl Boronic Acids using P(C₆H₅)(2-C₆H₄Cl)₂ as the Supporting Ligand. M. R. Pramick, S. M. Rosemeier, M. T. Beranek, S. B. Nickse, J. J. Stone, R. A. Stockland Jr., S. M. Baldwin, and Margaret E. Kastner Organometallics 2003, 22, 523.

Direct Observation of P(O)-C(sp³) Bond Formation from (N^ÇN)PdMe(P(O)(OPh)₂) Complexes. Rate Enhancement of reductive elimination by addition of Triarylphosphines. A. M. Levine, R. A. Stockland Jr., R. Clark, and I. A. Guzei, Organometallics 2002, 21, 3278.