Organic Syntheses, Volume 96

The current volume continues the tradition of the Organic Syntheses series, providing carefully checked and edited experimental procedures that describe important synthetic methods, transformations, reagents, and synthetic building blocks or intermediates with demonstrated utility in organic synthesis. These significant and interesting procedures should prove worthwhile to many synthetic chemists working in increasingly diverse areas. A trusted guide for professionals in organic and medicinal chemistry in academia, government, and industries, including pharmaceuticals, fine chemicals, agrochemicals, and biotechnological products.

Discussion Addendum for: 4-Nonylbenzoic Acid 1 Alois Fürstner Late-Stage Deoxyfluorination of Phenols with PhenoFluorMix 16 Junting Chen and Tobias Ritter Nickel-Catalyzed Cross-Coupling of 2-Methoxynaphthalene with Methyl 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzoate 36 Yuki Kawashima, Takayuki Furukawa, Naoto Chatani and Mamoru Tobisu Discussion Addendum for: Lithium Amides as Homochiral Ammonia Equivalents for Conjugate Additions to α,β-Unsaturated Esters: Asymmetric Synthesis of (S)-β-Leucine 53 Stephen G. Davies, Ai M. Fletcher, Paul M. Roberts, and James E. Thomson Synthesis of 2,3-Diaryl-2H-azirines via Cs2CO3-Mediated Cyclization of Ketoxime Acetates 66 Mi-Na Zhao and Zheng-Hui Guan Discussion Addendum for: The Direct Acyl-Alkylation of Arynes. Preparation of Methyl 2- (2-acetylphenyl)acetate 80 Austin C. Wright and Brian M. Stoltz Discussion Addendum for: Convenient Preparation of 3-Ethoxycarbonyl Benzofurans from Salicylaldehydes and Ethyl Diazoacetate 98 Mizzanoor Rahaman and M. Mahmun Hossain Discussion Addendum for: Phosphine-Catalyzed [4 + 2] Annulation: Synthesis of Ethyl 6-Phenyl-1-tosyl-1,2,5,6-tetrahydropyridine-3-carboxylate 110 Aslam C. Shaikh and Ohyun Kwon Discussion Addendum for: Protection of Alcohols using 2-Benzyloxy-1-methylpyridinium Trifluoromethanesulfonate: Methyl (R)-(-)-3-Benzyloxy-2-methyl Propanoate 124 Harvey F. Fulo, Philip A. Albiniak, and Gregory B. Dudley Synthesis of 4-Methylbenzoate(2′,4′,6′-trimethoxy-phenyl)iodonium Tosylate 137 Thomas L. Seidl, Aaron Moment, Charles Orella, Thomas Vickery, and David R. Stuart Gold-Catalyzed Oxidative Coupling of Arenes and Arylsilanes 150 Chris Nottingham, Verity Barber, and Guy C. Lloyd-Jones Discussion Addendum for: Preparation of Enantioenriched Homoallylic Primary Amines 179 Miguel Yus Discussion Addendum for: Synthesis of Ynamides by Copper-Mediated Coupling of 1,1-Dibromo-1-alkenes with Nitrogen Nucleophiles. Preparation of 4-Methyl-N-(2-phenylethynyl)-N-(phenylmethyl)benzenesulfonamide 195 Cédric Theunissen, Pierre Thilmany, Mounsef Lahboubi, Nicolas Blanchard, and Gwilherm Evano Discussion Addendum for: Phosphine-Catalyzed [3 + 2] Annulation: Synthesis of Ethyl 5-(tert-Butyl)-2-phenyl-1-tosyl-3-pyrroline-3-carboxylate 214 Aslam C. Shaikh and Ohuyn Kwon Discussion Addendum for: Synthesis of Highly Enantiomerically Enriched Amines by Asymmetric Transfer Hydrogenation of N-(tert-Butylsulfinyl) Imines 232 Miguel Yus Synthesis of Chiral Diamine Ligands for Nickel-catalyzed Asymmetric Cross-couplings of Alkylchloroboronate Esters with Alkylzincs: 1R,2R)-N,N’-Dimethyl-1,2-bis(2-methylphenyl)-1,2-diaminoethane 245 Yusuke Masuda and Gregory C. Fu Preparation of 5-(Triisopropylalkynyl) dibenzo[b,d] thiophenium triflate 258 Bernd Waldecker, Kevin Kafuta, and Manuel Alcarazo Three-Step Synthesis of 2-(Diiodomethyl)-4,4,5,5-tetramethyl- 1,3,2-dioxaborolane from Dichloromethane 277 Morgane Sayes, Guillaume Benoit, and André B. Charette Discussion Addendum for: Allylic Oxidation Catalyzed by Dirhodium(II) Tetrakis[ε-caprolactamate] of tert-Butyldimethylsilylprotected trans-Dehydroandrosterone 300 Yong-Liang Su, Luca De Angelis and Michael P. Doyle Preparation of (R)-3-(3,5-Bistrifluoromethylphenyl)-1,1’-bi-2-naphthol 312 Yusuke Kobayashi, Atsushi Matsuda, Tomoya Ushimaru, and Toshiro Harada Catalytic Enantioselective Addition of an In-Situ Prepared Aryltitanium Reagent to p-Chloroacetophenone: (R)-(+)-1-(4-Chlorophenyl)-1-m-tolylethanol 333 Yusuke Kobayashi, Atsushi Matsuda, Tomoya Ushimaru, and Toshiro Harada Stereoselective Synthesis of (R)-((R)-1-Phenyl-2,2,2-trichloroethyl)-2-(2-bromophenyl)aziridine-1-carboxylate 351 Hélène Lebel and Henri Piras Discussion Addendum for: Preparation of (R,R)-1,2:4,5-Diepoxypentane 361 Nicholas Sizemore and Scott D. Rychnovsky (R)-N,N’-Dimethyl-1,1’-binaphthyldiamine 382 Scott E. Denmark and Pavel Ryabchuk Preparation of a Diisopropylselenophosphoramide Catalyst and its Use in Enantioselective Sulfenoetherification 400 Scott E. Denmark, Pavel Ryabchuk, Hyung Min Chi, and Anastassia Matviitsuk anti-1,2,2,3,4,4-Hexamethylphosphetane 1-Oxide 418 Trevor V. Nykaza, Julian C. Cooper, and Alexander T. Radosevich Facile Reduction of Amides Using Nickel Catalysis: Reduction of 12-Aminododecanolactam 436 Bryan J. Simmons, Melissa Ramirez, and Neil K. Garg Preparation of 2,4,5,6-Tetra(9H-carbazol-9-yl)isophthalonitrile 455 Saskia M. Engle, Takisha R. Kirkner, and Christopher B. Kelly Discussion Addendum for: Fluorobis(phenylsulfonyl)methane (FBSM) 474 Xanath Ispizua-Rodriguez, Vinayak Krishnamurti, Mathew Coe, and G. K. Surya Prakash Synthesis of 5-Hydroxy-4-methoxy-2-methylpyrylium Trifluoromethanesulfonate from Kojic Acid 494 Nana B. Agyemang and Ryan P. Murelli Iridium-Catalyzed Reductive Coupling of Grignard Reagents and Tertiary Amides 511 Pablo Gabriel, Lan-Gui Xie, and Darren J. Dixon Synthesis of Chiral Tetramic Acids: Preparation of (S)-5-Benzylpyrrolidine-2,4-dione from L-Phenylalanine Methyl Ester Hydrochloride 528 Kyle M. Lambert, Austin W. Medley, Amy C. Jackson, Lauren E. Markham, and John L. Wood Synthesis of 8-Hydroxygeraniol 586 Francesca M. Ippoliti, Joyann S. Barber, and Neil K. Garg