Silicon-Based Cross-Coupling Reactions

[374] Understanding Site Selectivity in the Palladium-Catalyzed Cross-Coupling of Allenylsilanolates (with A. Ambrosi) Synlett 2017, 28, 2415-2420.

[361] Why You Really Should Consider Using Palladium-Catalyzed Cross-Coupling of Silanols and Silanolates (with A. Ambrosi) Org. Process Res. Dev. 2015, 19, 982-994.

[360] Mechanistic Significance of the Si-O-Pd Bond in the Palladium-Catalyzed Cross-Coupling Reactions of Arylsillanolates (with S. A. Tymonko, R. C. Smith, A. Ambrosi, M. H. Ober, and H. Wang) J. Am. Chem. Soc. 2015, 137, 6200-6218. [PMC4442671]

[359] Mechanistic Significance of the Si-O-Pd Bond in the Palladium-Catalyzed Cross-Coupling Reactions of Alkenylsilanolates (with S. A. Tymonko, R. C. Smith, and A. Ambrosi) J. Am. Chem. Soc. 2015, 137, 6192-6199. [PMC442670]

[356] Development of Chiral Bis-hydrazone Ligands for the Enantioselective Cross-Coupling Reactions of Aryldimethylsilanolates (with W. –T. T. Chang, K. N. Houk, and P. Liu) J. Org. Chem. 2015, 80, 313-366.

[332] Palladium-Catalyzed Cross-Coupling of (Z)-1-Heptenyldimethylsilanol with 4-Iodoanisole: (Z)-(1-Heptenyl)-4-Methoxybenzene (with J. H. –C. Liu) Org. Synth. 2011, 88, 102-108.

[330] γ-Selective Cross-Coupling of Allylic Silanolate Salts with Aromatic Bromides Using Trialkylphosphonium Tetrafluoroborate Salts Prepared Directly from Phosphine•Borane Adducts (with N. S. Werner) Org. Lett. 2011, 13, 4596-4599.

[327] Probing the Electronic Demands of Transmetalation in the Palladium-Catalyzed Cross-Coupling of Arylsilanolates (with R. C. Smith and W. –T. T. Chang) Tetrahedron, 2011, 67, 4391-4396.

[326] Cross-Coupling Reactions of Alkenylsilanols with Fluoroalkylsulfonates: Development and Optimization of a Mild and Stereospecific Coupling Process (with C. S. Regens) Tetrahedron Lett. 2011, 52, 2165-2168.

[324] Stereocontrolled Total Syntheses of Isodomoic Acids G and H via a Unified Strategy (with J. H.-C. Liu and J. M. Muhuhi) J. Org. Chem. 2011, 76, 201-215.

[323] Sequential Processes in Palladium-Catalyzed Silicon-Based Cross-Coupling (with J. H.-C. Liu) Isr. J. Chem. 2010, 50, 577-587.

[319] Development of a General, Sequential, Ring-Closing Metathesis/Intramolecular Cross-Coupling Reaction for the Synthesis of Polyunsaturated Macrolactones (with J. M. Muhuhi) J. Am. Chem. Soc. 2010, 132, 11768-11778.

[315] Total Synthesis of (+)-papulacandin D (with T. Kobayashi and C. S. Regens) Tetrahedron 2010, 66, 4745-4759.

[314] Silicon-Based Cross-Coupling Reactions in the Total Synthesis of Natural Products (with J. H.-C. Liu) Angew. Chem. Int. Ed. 2010, 49, 2978-2986.

[313] On the Stereochemical Course of Palladium-Catalyzed Cross-Coupling of Allylic Silanolate Salts with Aromatic Bromides (with N. S. Werner) J. Am. Chem. Soc. 2010, 132, 3612-3620.

[312] Mechanistic Duality in Palladium-Catalyzed Cross-Coupling Reactions of Aryldimethylsilanolates. Intermediacy of an 8-Si-4 Arylpalladium(II) Silanolate (with R. C. Smith) J. Am. Chem. Soc. 2010, 132, 1243-1245.

[308] Total Synthesis of Isodomoic Acids G and H (with J. H. –C. Liu and J. M. Muhuhi) J. Am. Chem. Soc. 2009, 131, 14188-14189.

[305] Vinylation with Inexpensive Silicon-Based Reagents: Preparation of 3- Vinylquinoline and 4-Vinylbenzophenone (with C. R. Butler) Org. Synth. 2009, 86, 274-286.

[304] The Interplay of Invention, Discovery, Development, and Application in Organic Synthetic Methodology J. Org. Chem. 2009, 74, 2915-2927.

[303] Preparation of 2,3-Disubstituted Indoles by Sequential Larock Heteroannulation and Silicon-Based Cross-Coupling Reactions (with J. D. Baird) Tetrahedron 2009, 65, 3120-3129.

[301] Cross-Coupling Reactions of Aromatic and Heteroaromatic Silanolates with Aromatic and Heteroaromatic Halides (with R.C. Smith, W-t.T. Chang, and J.M. Muhuhi) J. Am. Chem. Soc. 2009, 131, 3104-3118.

[299] Palladium- (and nickel-) catalyzed vinylation of aryl halides (with C. R. Butler) Chem. Commun. 2009, 20-33.

[297] Cross-Coupling of Aromatic Bromides with Allylic Silanolate Salts (with N. S Werner) J. Am. Chem. Soc. 2008, 130, 16382-16393.

[296] Palladium-Catalyzed Cross-Coupling Reactions of Organosilanols and their Salts: A Practical Alternative to Boron- and Tin-based Methods (with C. S. Regens) Acc. Chem. Res. 2008, 41, 1486-1499..

[294] Total Synthesis of Papulacandin D (in Japanese) (with T. Kobayashi and C. S. Regens) Yuki Gosei Kagaku Kyosashi 2008, 66, 616-628.

[288] Vinylation of Aromatic Halides Using Inexpensive Organosilicon Reagents Illustration of Design of Experiment Protocols (with C. R. Butler) J. Am. Chem. Soc. 2008, 130, 3690-3704.

[284] Palladium-Catalyzed Cross-Coupling of Five-Membered Heterocyclic Silanolates (with J. D. Baird and C. S. Regens) J. Org. Chem. 2008, 73, 1440-1455.

[273] Phosphine Oxides as Stabilizing Ligands for the Palladium-Catalyzed Cross-Coupling of Potassium Aryldimethylsilanolates (with R. C. Smith and S. A. Tymonko) Tetrahedron 50th Anniversary Special Edition, 2007, 63, 5730-5738.

[271] Sequential Silylcarbocyclization/Silicon-Based Cross-Coupling Reactions (with J.H.-C. Liu) J. Am. Chem. Soc. 2007, 129, 3737-3744.

[270] Total Synthesis of Papulacandin D (with C. S. Regens and T. Kobayashi) J. Am. Chem. Soc. 2007, 129, 2774-2776.

[269] Stereospecific Palladium-Catalyzed Cross-Coupling of (E)- and (Z)-Alkenylsilanolates with Aryl Chlorides (with J. M. Kallemeyn) J. Am. Chem. Soc. 2006, 128, 15958-15959.

[267] Reduction of Allylpalladium(II)chloride Dimer by Formation of Allyloxysilanes (with R. C. Smith) Synlett, 2006, 18, 2921-2928.

[266] A Qualitative Examination of the Effects of Silicon Substituents on the Efficiency of Cross-Coupling Reactions (with L. Neuville, M. E. L. Christy, and S. A. Tymonko) J. Org. Chem. 2006, 71, 8500-8509.

[262] Palladium-Catalyzed Cross-Coupling Reactions of Silanolates: A Paradigm Shift in Silicon-Based Cross-Coupling Reactions (with J. D. Baird) Chem. Eur. J. 2006, 12, 4954-4963.

[255] Palladium-Catalyzed Cross-Coupling Reactions of Heterocyclic Silanolates with Substituted Aryl Iodides and Bromides (with J. D. Baird) Org. Lett. 2006, 8, 793-795.

[252] Vinylation of Aryl Bromides Using an Inexpensive Vinylpolysiloxane (with C. R. Butler) Org. Lett. 2006, 8, 63-66.

[241] Sequential Cross-Coupling of 1,4-Bissilylbutadienes: Synthesis of Unsymmetrical 1,4-Disubstituted 1,3-Butadienes (with S. A. Tymonko) J. Am. Chem. Soc .2005, 127, 8004-8005.

[240] Synthesis of 3,4,5-Trisubstituted Isoxazoles via Sequential [3+2] Cycloaddition/Silicon-Based Cross-Coupling Reactions. (with J. M. Kallemeyn) J. Org. Chem. 2005, 70, 2839-2842.

[238] Palladium-Catalyzed Cross-Coupling Reactions of Substituted Aryl(dimethyl)silanols (with M. H. Ober) Adv. Synth. Catal. 2004, 346, 1703-1714.

[237] Platinum Catalyzed Hydrosilylation and Palladium Catalyzed Cross-Coupling: One-pot Hydroarylation of 1-Heptyne (with Z. Wang) Org. Synth. 2004, 81, 54-62.

[236] Palladium Catalyzed Cross-Coupling of (Z)-1-Heptenyldimethylsilanol with 4-iodoanisole: (Z)-1-Heptenyl)-4-methoxybenzene (with Z. Wang) Org. Synth. 2004, 81, 42-53.

[234] Total Synthesis of (+)-Brasilenyne. Application of an Intramolecular Silicon-Assisted Cross-Coupling Reaction (with S. M. Yang) J. Am. Chem. Soc. 2004, 126, 12432-12440.

[233] Palladium-Catalyzed Cross-Coupling Reactions of 2-Indolyldimethylsilanols with Substituted Aryl Halides (with J. D. Baird) Org. Lett. 2004, 6, 3649-3652.

[232] Sequential Ring-Closing Metathesis/Pd-Catalyzed, Si-Assisted Cross-Coupling Reactions: General Synthesis of Highly Substituted Unsaturated Alcohols and Medium-Sized Rings Containing a 1,3-cis-cis Diene Unit (with S.–M. Yang) Tetrahedron 2004, 60, 9695-9708.

[229] Cross-Coupling Reactions of Alkenylsilanolates. Investigation of the Mechanism and Identification of Key Intermediates through Kinetic Analysis (with R. F. Sweis) J. Am. Chem. Soc. 2004, 126, 4876-4882.

[228] Fluoride-Promoted Cross-Coupling Reactions of Alkenylsilanols. Elucidation of the Mechanism through Spectroscopic and Kinetic Analysis (with R. Sweis and D. Wehrli) J. Am. Chem. Soc. 2004, 126, 4865-4875.

[225] Organosilicon Reagents: Synthesis and Application to Palladium-Catalyzed Cross-Coupling Reactions (with M. H. Ober) Aldrichimica Acta 2003, 36, 75-85.

[224] Cross-Coupling of Alkynylsilanols with Aryl Halides Promoted by Potassium Trimethylsilanolate. (with S. A. Tymonko) J. Org. Chem. 2003, 68, 9151-9154.

[222] Palladium-Catalyzed Conjugate Addition of Organosiloxanes to alpha- beta -Unsaturated Carbonyl Compounds and Nitroalkenes (with N. Amishiro) J. Org. Chem. 2003, 68, 6997-7003.

[221] Palladium-Catalyzed Silylation of Aryl Bromides Leading to Functionalized Aryldimethylsilanols (with J. M. Kallemeyn) Org. Lett. 2003, 5, 3483-3486.

[217] Tandem Intramolecular Silylformylation and Silicon-Assisted Cross-Coupling Reactions. Synthesis of Geometrically Defined a,b- Unsaturated Aldehydes (with T. Kobayashi) J. Org. Chem. 2003, 68, 5153-5159.

[214] Cross-Coupling Reactions of Arylsilanols with Substituted Aryl Halides (with M. H. Ober) Org. Lett. 2003, 5, 1357-1360.

[213] Intramolecular Syn and Anti Hydrosilylation and Silicon-Assisted Cross-Coupling: Highly Regio- and Stereoselective Synthesis of Trisubstituted Allylic Alcohols (with W. Pan) Org. Lett. 2003, 5, 1119-1122.

[209] Intramolecular Silicon-Assisted Cross-Coupling: Total Synthesis of (+)-Brasilenyne (with S.-M. Yang) J. Am. Chem. Soc. 2002, 124, 15196-15197.

[207] Cross-Coupling Reactions of Organosilicon Compounds: New Concepts and Recent Advances (with R. Sweis) Chem. Pharm. Bull. 2002, 50, 1531-1541.

[206] Intramolecular Anti-Hydrosilylation and Silicon-Assisted Cross-Coupling: Highly Regio- and Stereoselective Synthesis of Trisubstituted Homoallylic Alcohols (with W. Pan) Org. Lett. 2002, 4, 4163-4166.

[203] Design and Implementation of New, Silicon-Based, Cross-Coupling Reactions: Importance of Silicon–Oxygen Bonds (with R. F. Sweis) Acc. Chem. Res. 2002, 35, 835-846.

[202] Cross-Coupling Reactions of Alkenylsilanols with Fluoroalkylsulfonates (with R. F. Sweis) Org. Lett. 2002, 4, 3771-3774.

[199] Efficient and Stereoselective Cross-Coupling with Highly Substituted Alkenylsilanols (with W. Pan) J. Organomet. Chem. 2002, 653, 98-104.

[195] Intramolecular Silicon-Assisted Cross-Coupling Reactions: General Synthesis of Medium-Sized Rings Containing a 1,3-cis-cis Diene Unit (with S.-M. Yang) J. Am. Chem. Soc. 2002, 124, 2102-2103.

[187] Fluoride-Free Cross-Coupling of Organosilanols (with R. F. Sweis) J. Am. Chem. Soc. 2001, 123, 6439-6440.

[183] Sequential Ring-Closing Metathesis and Silicon-Assisted Cross-Coupling Reactions: Stereocontrolled Synthesis of Highly Substituted Unsaturated Alcohols (with S.-M. Yang) Org. Lett. 2001, 3, 1749-1752.

[182] Cross-coupling of Vinylpolysiloxanes with Aryl Iodides (with Z. Wang) J. Organomet. Chem. 2001, 624, 372-375.

[181] Highly Stereoselective Hydrocarbation of Terminal Alkynes via Pt-Catalyzed Hydrosilylation/Pd-Catalyzed Cross-Coupling Reactions (with Z. Wang) Org. Lett. 2001, 3, 1073-1076.

[180] Intramolecular Hydrosilylation and Silicon-Assisted Cross-Coupling: An Efficient Route to Trisubstituted Homoallylic Alcohols (with W. Pan) Org. Lett. 2001, 3, 61-64.

[178] Mild and General Cross-Coupling of (alpha-Alkoxyvinyl)-silanols and –silyl Hydrides (with L. Neuville) Org. Lett. 2000, 2, 3221-3224.

[174] Convergence of Mechanistic Pathways in the Palladium(0)-Catalyzed Cross-Coupling of Alkenylsilacyclobutanes and Alkenylsilanols (with D. Wehrli and J. Y. Choi) Org. Lett. 2000, 2, 2491-2494.

[173] 1-Methyl-1-Vinyl- and 1-Methyl-1-(2-propenyl)silacyclobutane. Reagents for Palladium-Catalyzed Cross-Coupling Reactions of Aryl Halides (with Z. Wang) Synthesis 2000, 999-1003.

[168] Highly Stereospecific, Palladium-Catalyzed Cross–Coupling of Alkenylsilanols (with D. Wehrli) Org. Lett. 2000, 2, 565-568.