2010-2014

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2014

Mechanism of SmI2/Amine/H2O-Promoted Chemoselective Reductions of Carboxylic Acid Derivatives (Esters, Acids, and Amides) to Alcohols
Szostak, M.; Spain, M.; Eberhart, A. J.; Procter,D. J.
J. Org. Chem. 2014, 79, 11988

Switching between Reaction Pathways by an Alcohol Cosolvent Effect: SmI2−Ethylene Glycol vs SmI2−H2O Mediated Synthesis of Uracils
Szostak, M.; Spain, M.; Sautier, B.; Procter, D. J.
Org. Lett. 2014, 16, 5694

Selective Synthesis of α,α-Dideuterio Alcohols by the Reduction of Carboxylic Acids Using SmI2 and D2O as Deuterium Source under SET Conditions
Szostak, M.; Spain, M.; Procter, D. J.
Org. Lett. 2014, 16, 5052

SmI2-H2O-Mediated 5-exo/6-exo Lactone Radical Cyclisation Cascades
Yalavac, I.; Lyons, S. E.; Webb, M. R.; Procter, D. J.
Chem. Commun. 2014, 50, 12863
Invited contribution to web themed issue celebrating Richard Taylor's 65th birthday

Cu(I)-NHC Catalyzed Silylation of Allenes: Diastereoselective Three Component Coupling with Aldehydes
Rae, J.; Hu, Y-C; Procter, D. J.
Chem. –Eur. J. 2014, 20, 13143
Highlighted in Synfacts 2014, 10(12), 1313

Ketyl-Type Radicals from Cyclic and Acyclic Esters are Stabilized by SmI2(H2O)n – The Role of SmI2(H2O)n in Post-Electron Transfer Steps
Szostak, M.; Spain, M.; Procter, D. J.
J. Am. Chem. Soc. 2014, 136, 8459

Evaluating a Sodium Dispersion Reagent for the Bouveault-Blanc Reduction of Esters
An, J.; Work, N. D.; Kenyon, C.; Procter, D. J.
J. Org. Chem. 2014, 79, 6743

Synthesis and Synthetic Chemistry of Pleuromutilin
Fazakerley, N. J.; Procter, D. J.
Tetrahedron 2014, 70, 6911

Mechanistic Investigation of the Selective Reduction of Meldrum's Acids to b-Hydroxy Acids using SmI2 and H2O
Szostak, M.; Lyons, S. E.; Spain, M.; Procter, D. J.
Chem. Commun. 2014, 50, 8391
Invited contribution to web themed issue on 'Non-Innocent Ligands'

Cross-Coupling Reactions Using Samarium(II) Iodide
Szostak, M.; Fazakerley, N. J.; Parmar, D.; Procter, D. J.
Chem. Rev. 2014, 114, 5959

A Sm(II)-Mediated Cascade Approach to Dibenzoindolo[3,2-b]carbazoles: Synthesis and Evaluation
Levick, M. T.; Grace, I.; Dai, S-Y.; Kasch, N.; Muryn, C.; Lambert, C.; Turner, M. L.; Procter, D. J.
Org. Lett. 2014, 16, 2292
Highlighted in Synfacts 2014, 10(7), 0694

On the Role of Pre- and Post-Electron Transfer Steps in the SmI2/amine/H2O-Mediated Reduction of Esters: New Mechanistic Insights and Kinetic Studies
Szostak, M.; Spain, M.; Procter, D. J.
Chem. –Eur. J. 2014, 20, 4222

Determination of the Effective Redox Potentials of SmI2, SmBr2, SmCl2, and their Complexes with Water by Reduction of Aromatic Hydrocarbons. Reduction of Anthracene and Stilbene by Samarium(II) Iodide–Water Complex
Szostak, M.; Spain, M.; Procter, D. J.
J. Org. Chem. 2014, 79, 2522

Highly Chemoselective Reduction of Amides (Primary, Secondary, Tertiary) to Alcohols using SmI2/Amine/H2O under Mild Conditions
Szostak, M.; Spain, M.; Eberhart, A. J.; Procter, D. J.
J. Am. Chem. Soc. 2014, 136, 2268
Highlighted in Synfacts 2014, 10(5), 0527

Structural analysis and reactivity of unusual tetrahedral intermediates enabled by SmI2-mediated reduction of barbituric acids: vinylogous N-acyliminium additions to α-hydroxy-N-acyl-carbamides
Szostak, M.; Sautier, B.; Procter, D. J.
Chem. Commun. 2014, 50, 2518

Electron Transfer Reduction of Nitriles Using SmI2–Et3N–H2O: Synthetic Utility and Mechanism
Szostak, M.; Sautier, B.; Spain, M.; Procter, D. J.
Org. Lett. 2014, 16, 1092

Stereoselective Capture of N-Acyliminium Ions Generated from α-Hydroxy-N-acylcarbamides: Direct Synthesis of Uracils from Barbituric Acids Enabled by SmI2 Reduction
Szostak, M.; Sautier, B.; Procter, D. J.
Org. Lett. 2014, 16, 452

Cu(I)–NHC Catalyzed Asymmetric Silyl Transfer to Unsaturated Lactams and Amides
Pace, V.; Rae, J. P.; Procter, D. J.
Org. Lett. 2014, 16, 476
Highlighted in Synfacts 2014, 10(4), 0400

2013

Substrate-Directable Electron Transfer Reactions. Dramatic Rate Enhancement in the Chemoselective Reduction of Cyclic Esters Using SmI2–H2O: Mechanism, Scope, and Synthetic Utility
Szostak, M.; Spain, M.; Choquette, K. A.; Flowers, II, R. A.; Procter, D. J.
J. Am. Chem. Soc. 2013, 135, 15702
Highlighted in Synform

Selective Reduction of Barbituric Acids Using SmI2/H2O: Synthesis, Reactivity, and Structural Analysis of Tetrahedral Adducts
Szostak, M.; Sautier, B.; Spain, M.; Behlendorf, M.; Procter, D. J.
Angew. Chem. Int. Ed. 2013, 52, 12559

Recent advances in the chemoselective reduction of functional groups mediated by samarium(II) iodide: a single electron transfer approach
Szostak, M.; Spain, M.; Procter, D. J.
Chem. Soc. Rev. 2013, 42, 9155

Nucleophilic ortho-Allylation of Pyrroles and Pyrazoles: An Accelerated Pummerer/Thio-Claisen Rearrangement Sequence
Eberhart, A. J.; Cicoira, C.; Procter, D. J.
Org. Lett. 2013, 15, 3994

Development of an additive-controlled, SmI2-mediated stereoselective sequence: Telescoped spirocyclisation, lactone reduction and Peterson elimination
Sautier, B.; Collins, K. D.; Procter, D. J.
Beilstein J. Org. Chem. 2013, 9, 1443
Invited contribution to BJOC thematic series: "Organic Free Radical Chemistry", ed. Prof. Corey Stephenson

Uncovering the Importance of Proton Donors in TmI2-Promoted Electron Transfer: Facile C-N Bond Cleavage in Unactivated Amides
Szostak, M.; Spain, M.; Procter, D. J.
Angew. Chem. Int. Ed. 2013, 52, 7237
Highlighted in Synfacts 2013, 9(9), 1001
Organic Chemistry Highlights

SmI2-mediated couplings of a-amino acid derivatives. Formal synthesis of (-)-pumiliotoxin 251D and (+/-)-epiquinamide
Pinho, V. D.; Procter, D. J.; Burtoloso, A. C. B.
Org. Lett. 2013, 15, 2434

NHC-Cu(I) Catalysed Asymmetric Conjugate Silyl Transfer to Unstaurated Lactones: Application in Kinetic Resolution
Pace, V.; Rae, J. P.; Harb. H. Y.;Procter, D. J.
Chem. Commun. 2013, 49, 5150
Highlighted in Synfacts 2013, 9(9), 983

Total synthesis of (+)-pleuromutilin
Fazakerley, N. J.; Helm, M. D.; Procter, D. J.
Chem. –Eur. J. 2013, 19, 6718
Selected for Cover Art
Organic Chemistry Highlights

Dihydropyrroloindoledione-based copolymers for organic electronics
Rumer, J. W.; Dai, S-Y.; Levick, M.; Kim, Y.; Madec, M-B.; Ashraf, R. S.; Huang, Z.; Rossbauer, S.; Schroeder, B.; Biniek, L.; Watkins, S. E.; Anthopoulos, T. D.; Janssen, R. A. J.; Durrant, J. R.; Procter, D. J.; McCulloch, I.
J. Mater. Chem. C 2013, 1, 2711

Nucleophilic ortho-propargylation of aryl sulfoxides: an interrrupted Pummerer/allenyl thio-Claisen rearrangement sequence
Eberhardt, A. J.; Procter, D. J.
Angew. Chem. Int. Ed. 2013, 52, 4008

Synthesis of two dihydropyrroloindoledione-based copolymers for organic electronics
Rumer, J. W.; Dai, Sheng-Yao; Levick, M.; Biniek, L.; Procter, D. J.; McCulloch, I.
J. Polym. Sci. A Polym. Chem. 2013, 51, 1285

2012

Phase Tag-Assisted Synthesis of Benzo[b]carbazole End-Capped Oligothiophenes
Levick, M. T.; Coote, S. C.; Grace, I.; Lambert, C.; Turner, M. L.; Procter, D. J. Org. Lett. 2012, 14, 5744

Beyond Samarium Diiodide: Vistas in Reductive Chemistry Mediated by Lanthanides(II)
Szostak, M.; Procter, D. J.
Angew. Chem. Int. Ed. 2012, 51, 9238

Lactone radical cyclizations and cyclization cascades mediated by SmI2–H2O
Parmar, D.; Matsubara, H.; Price, K.; Spain, M.; Procter, D. J.
J. Am. Chem. Soc. 2012, 134, 12751

Recent advances in the chemistry of SmI2–H2O
Sautier, B.; Procter, D. J.
Chimia 2012, 66, 399
Invited contribution to Special Issue. Selected for Cover Art

A General Electron Transfer Reduction of Lactones Using SmI2–H2O
Szostak, M.; Collins, K. D.; Fazakerley, N. J.; Spain, M.; Procter, D. J.
Org. Biomol. Chem. 2012, 10, 5820
Invited contribution to "Organic & Biomolecular Chemistry 10th Anniversary" Collection

Selective synthesis of 3-hydroxy acids from Meldrum’s acids using SmI2-H2O
Szostak, M.; Spain, M.; Procter, D. J.
Nat. Protocol 2012, 7, 970

Preparation of Samarium(II) Iodide: Quantitative Evaluation of the Effect of Water, Oxygen, and Peroxide Content, Preparative Methods, and the Activation of Samarium Metal
Szostak, M.; Spain, M.; Procter, D. J.
J. Org. Chem. 2012, 77, 3049

Electron transfer reduction of carboxylic acids using SmI2-H2O-Et3N
Szostak, M.; Spain, M.; Procter, D. J.
Org. Lett. 2012, 14, 840

SmI2-Mediated Carbonyl-Alkene Couplings for the Synthesis of Small Carbocyclic Rings
Harb, Y. H.; Procter, D. J.
Synlett 2012, 23, 6

Selective Reductive Transformations Using Samarium Diiodide-Water
Szostak, M.; Spain, M.; Parmar, D.; Procter, D. J.
Chem Commun. 2012, 48, 330

Radical Cyclization Cascades of Unsaturated Meldrum's Acid Derivatives
Sautier, B.; Lyons, S. E.; Webb, M. R.; Procter, D. J.
Org. Lett. 2012, 14, 146

Organic Synthesis Using Samarium Diiodide
Coote, S. C.; Flowers II, R. A.; Skrydstrup, T.; Procter, D. J.
in Encyclopedia of Radicals in Chemistry, Biology and Materials 2012, John Wiley & Sons, Ltd.

2011

Nucleophilic Ortho Allylation of Aryl and
Heteroaryl Sulfoxides
Eberhart, A. J.; Imbriglio, J. E.; Procter, D. J.
Org. Lett. 2011, 13, 5882

Synthesis of the ABH rings of ecteinascidin 597 using a connective Pummerer-type cyclisation
Smith, L. H. S.; Nguyen, T. T.; Sneddon, H. F.; Procter, D. J.
Chem. Commun. 2011, 47, 10821

Electron transfer reduction of unactivated esters using SmI2-H2O
Szostak, M.; Spain, M.; Procter, D. J.
Chem. Commun. 2011, 47, 10254

Concise Syntheses of Strychnine and Englerin A: the Power of Reductive Cyclizations Triggered by Samarium Iodide for the Rapid Assembly of Old and New Targets
Szostak, M.; Procter, D. J.
Angew. Chem. Int. Ed. 2011, 50, 7737

Exploiting Sm(II) and Sm(III) in SmI2-initiated reaction cascades: application in a tag removal-cyclisation approach to spirooxindole scaffolds
Coote, S. C.; Quenum S.; Procter , D. J.
Org. Biomol. Chem. 2011, 9, 5104

Reductive Cyclization Cascades of Lactones Using SmI2–H2O
Parmar, D.; Price, K.; Spain, M.; Matsubara, H.;Bradley, P. A.; Procter, D. J.
J. Am. Chem. Soc. 2011, 133, 2418

A stereoselective, Sm(II)–mediated approach to decorated cis–hydrindanes: synthetic studies on faurinone and pleuromutilin
Findley, T. J. K.; Sucunza, D.; Miller, L. C.; Helm, M. D.; Helliwell, M.; Davies, D. T.; Procter, D. J.
Org. Biomol. Chem. 2011, 9, 2433
Invited contribution to the Athel Beckwith Special issue

2010

Product Class 17: Acyclic Hemiacetals, Lactols, and Carbonyl Hydrates
Coote, S. C.; Smith, L. H. S.; Procter, D. J.
Science of Synthesis Section 29.17, Thieme, Volume Update Editor, Procter, D. J. 2010, 417.
Invited Volume Update Editor

Product Class 18: 1,1–Diacyloxy compounds
Smith, L. H. S.; Coote, S. C.; Procter, D. J.
Science of Synthesis Section 29.18, Thieme, Volume Update Editor, Procter, D. J. 2010, 475.
Invited Volume Update Editor

SmI2–mediated radical cyclizations directed by a C−Si bond
Harb, H. Y.; Collins, K. D.; Garcia Altur, J. V.; Bowker, S.; Campbell, L.; Procter, D. J. Org. Lett. 2010, 12, 5446

Dynamic Ligand Exchange in Reactions of Samarium Diiodide
Sadasivam, D. V.; Teprovich Jr, J. A.; Procter, D. J.; Flowers II, R. A.
Org. Lett. 2010, 12, 4140

Selective reductions of cyclic 1,3-diesters using SmI2 and H2O
Collins, K. D.; Oliveira, J. M.; Guazzelli, G.; Sautier, B.; De Grazia, S.; Matsubara, H.; Helliwell, M.; Procter, D. J.
Chem. –Eur. J. 2010, 16, 10240

A Stereoselective Cyclization Cascade Mediated by SmI2-H2O: Synthetic Studies towards Stolonidiol
Baker, T. M.; Sloan, L. A.; Choudhury, L. H.; Murai, M.; Procter, D. J.
Tetrahedron: Asymmetry 2010, 21, 1246
Invited contribution to the Henri Kagan Special issue

Beyond the Pummerer Reaction: Recent Developments in Thionium Ion Chemistry
Smith, L. H. S.; Coote, S. C.; Sneddon, H. F.; Procter, D. J.
Angew. Chem. Int. Ed. 2010, 49, 5832