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Synthetic Communications

An International Journal for Rapid Communication of Synthetic Organic Chemistry

Volume 26, 1996 - Issue 7

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Synthesis of N-t-Boc-4-S-t-Butyl-L-thiophenylalanine via Palladium Catalyzed Cross-Coupling Reaction of N-t-Boc-4-Iodo-L-phenylalanine with t-Butylthiol or Sodium t-Butylthiolate

Shyamala Rajagopalan Department of Biochemistry, Kansas State University, Manhattan, KS, 66506

Gary Radke Department of Biochemistry, Kansas State University, Manhattan, KS, 66506

Michelle Evans Department of Biochemistry, Kansas State University, Manhattan, KS, 66506

John M. Tomich Department of Biochemistry, Kansas State University, Manhattan, KS, 66506

Pages 1431-1440 | Received 30 Sep 1995, Published online: 15 Aug 2006

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https://doi.org/10.1080/00397919608003505

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Vikas Sikervar. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis 1 4 .

Sara R. Goldstein, Chen Liu, Martin K. Safo, Akito Nakagawa, Warren M. Zapol & Jeffrey D. Winkler. (2018) Design, Synthesis, and Biological Evaluation of Allosteric Effectors That Enhance CO Release from Carboxyhemoglobin. ACS Medicinal Chemistry Letters 9:7, pages 714-718.
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Jeffrey D. Rudolf & C. Dale Poulter. (2013) Tyrosine O -Prenyltransferase SirD Catalyzes S -, C -, and N -Prenylations on Tyrosine and Tryptophan Derivatives . ACS Chemical Biology 8:12, pages 2707-2714.
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Christina R. Forbes & Neal J. Zondlo. (2012) Synthesis of Thiophenylalanine-containing Peptides via Cu(I)-mediated Cross-Coupling. Organic Letters 14:2, pages 464-467.
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Irina P. Beletskaya & Valentine P. Ananikov. (2011) Transition-Metal-Catalyzed C−S, C−Se, and C−Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions. Chemical Reviews 111:3, pages 1596-1636.
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Irina P. Beletskaya & Valentine P. Ananikov. 2010. Catalyzed Carbon‐Heteroatom Bond Formation. Catalyzed Carbon‐Heteroatom Bond Formation 69 118 .

Laura E. Hagopian, Alison N. Campbell, James A. Golen, Arnold L. Rheingold & Chip Nataro. (2006) Synthesis and electrochemistry of late transition metal complexes containing 1,1′-bis(dicyclohexylphosphino)ferrocene (dcpf). The X-ray structure of [PdCl2(dcpf)] and Buchwald–Hartwig catalysis using [PdCl2(bisphosphinometallocene)] precursors. Journal of Organometallic Chemistry 691:23, pages 4890-4900.
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Xavier Moreau, Jean Marc Campagne, Gilbert Meyer & Anny Jutand. (2005) Palladium-Catalyzed C-S Bond Formation: Rate and Mechanism of the Coupling of Aryl or Vinyl Halides with a Thiol Derived from a Cysteine. European Journal of Organic Chemistry 2005:17, pages 3749-3760.
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Clotilde Mispelaere-Canivet, Jean-Francis Spindler, Stéphane Perrio & Pierre Beslin. (2005) Pd2(dba)3/Xantphos-catalyzed cross-coupling of thiols and aryl bromides/triflates. Tetrahedron 61:22, pages 5253-5259.
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Xavier Moreau & Jean-Marc Campagne. (2003) Palladium catalyzed thiol cross-coupling of cystein derivatives with aryl and alkenyl halides. Journal of Organometallic Chemistry 687:2, pages 322-326.
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Damien Prim, Jean-Marc Campagne, Delphine Joseph & Bruno Andrioletti. (2002) Palladium-catalysed reactions of aryl halides with soft, non-organometallic nucleophiles. Tetrahedron 58:11, pages 2041-2075.
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Teruyuki Kondo & Take-aki Mitsudo. (2000) Metal-Catalyzed Carbon−Sulfur Bond Formation. Chemical Reviews 100:8, pages 3205-3220.
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Sebastian Wendeborn, Alain De Mesmaeker, Wolfgang K.-D. Brill & Sabine Berteina. (2000) Synthesis of Diverse and Complex Molecules on the Solid Phase. Accounts of Chemical Research 33:4, pages 215-224.
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Bernd Kayser, Janina Altman, Heinrich Nöth, Jörg Knizek & Wolfgang Beck. (1998) Metal Complexes of Alkyne-Bridged α-Amino Acids. European Journal of Inorganic Chemistry 1998:11, pages 1791-1798.
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JACK H. LAI, THOMAS H. MARSILJE, SUN CHOI, SHRIKUMAR A. NAIR & DAVID G. HANGAUER. (2009) The design, synthesis and activity of pentapeptide pp60 c‐src inhibitors containing L‐phosphotyrosine mimics . The Journal of Peptide Research 51:4, pages 271-281.
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Louis S. Hegedus. (1998) Transition metals in organic synthesis: highlights for the year 1996. Coordination Chemistry Reviews 168, pages 49-175.
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Bernd Kayser, Janina Altman & Wolfgang Beck. (1997) Alkyne bridged α- amino acids by palladium mediated coupling of alkynes with N-t-Boc-4-iodo-phenylalanine methyl ester. Tetrahedron 53:7, pages 2475-2484.
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Renzo Rossi, Fabio Bellina & Luis Mannina. (1997) Selective palladium-mediated CarbonOxygen bond and CarbonSulfur bond forming reactions which involve functionalized Csp2-Hybridized halides or triflates and Csp-Hybridized halides. Tetrahedron 53:3, pages 1025-1044.
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S. RAJAGOPALAN, G. RADKE, M. EVANS & J. M. TOMICH. (2010) ChemInform Abstract: Synthesis of N‐t‐BOC‐4‐S‐t‐butyl‐L‐thiophenylalanine via Palladium‐ Catalyzed Cross‐Coupling Reaction of N‐t‐BOC‐4‐iodo‐L‐phenylalanine with t‐Butylthiol or Sodium t‐Butylthiolate.. ChemInform 27:32.
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Synthesis of N-t-Boc-4-S-t-Butyl-L-thiophenylalanine via Palladium Catalyzed Cross-Coupling Reaction of N-t-Boc-4-Iodo-L-phenylalanine with t-Butylthiol or Sodium t-Butylthiolate

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