Walsh, Patrick J. - The University of Pennsylvania

个人简介

Professional Experience 2005-present Professor of Chemistry, University of Pennsylvania 2008-2018 Alan MacDiarmid Term Chair 2002-2005 Associate Professor of Chemistry, University of Pennsylvania 1999-2002 Assistant Professor of Chemistry, University of Pennsylvania 1994-1999 Assistant Professor of Chemistry, San Diego State University Education 1991-1994 The Scripps Research Institute NSF Postdoctoral Fellow Postdoctoral Advisor Prof. K. Barry Sharpless 1991 University of California, Berkeley Ph.D in Chemistry Advisor Prof. Robert G. Bergman Thesis title “The Synthesis and Reactivity of Zirconium-Nitrogen Double and Single Bonds” 1986 B.A. in Chemistry, University of California, San Diego

研究领域

1. Novel palladium/nickel-catalyzed cross-coupling reactions involving C-C / C-S / C-N bonds formations 2. Development of catalysts for enantio- and diastereo- Selective C-C and C-S bond-formation. 3. Transition-metal-free radical chemistry of azaallyls promoted by base

近期论文

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Zheng, Z.; Walsh, P. J. Efficient Synthesis of Bulky 2,2’-Bipyridine and (S)-Pyridine-Oxazoline Ligands. Adv. Syn. & Catal. 2020, 362, ASAP. (DOI: 10.1002/adsc.202001218) Lin, T.; Gu, Y.; Qian, P.; Guan, H.; Walsh, P. J.; Mao, J. Nickel-catalyzed Reductive Coupling of Homoenolates and their Higher Homologues with Unactivated Alkyl Bromides. Nature Commun. 2020, 11, 5638. (DOI: 10.1038/s41467-020-19194-x) Hansen, A. S.; Liu, Z.; Chen, S.; Schumer, M.; Walsh, P. J.; Lester, M. I. Unraveling Conformer Specific Sources of Hydroxyl Radical Production from an Isoprene-derived Criegee Intermediate by Deuteration. J. Phys. Chem. A. 2020, 124, 4929–4938. (DOI: 10.1021/acs.jpca.0c02867) Vansco, M. F.; Caravan, R. L.; Pandit, S.; Zuraski, K.; Winiberg, F. A. F. Au, K.; Bhagde, T.; Trongsiriwat, N.; Walsh, P. J.; Osborn, D. L.; Percival, C. J.; Klippenstein, S. J.; Taatjes, C. A.; Lester, M. I. Formic Acid Catalyzed Isomerization and Adduct Formation of an Isoprene-derived Criegee Intermediate: Experimental and Theory, Phys. Chem. Chem. Phys. 2020, 22, 26796-26805 (DOI: 10.1039/d0cp05018k) Zhu, C.; Liu, Z.-Y.; Tang, L.; Zhang, H.; Zhang, Y.-F.; Walsh, P. J.; Feng, C. Migratory functionalization of unactivated alkyl bromides for construction of all-carbon quaternary centers via transposed tert-C-radicals. Nat. Commun.2020, 11, 4860. (DOI: 10.1038/s41467-020-18658-4) Yang, F.; Zou, D.; Chen, S.; Wang, H.; Zhao, Y.; Zhao, L.; Li, L.; Li, J.; Walsh, P. J. Transition Metal-Free Aroylation of Diarylmethanes with N-Bn-N-Boc Arylamides and N-Acylpyrroles. Adv. Syn. & Catal. 2020, 362, 3423-3430 (DOI: 10.1002/adsc.202000622) Wu, C.; McCollom, S. P.; Zheng, Z.; Zhang, J.; Sha, S.-C.; Li, M.; Walsh, P. J.; Tomson, N. C. Aryl Fluoride Activation Through Palladium-Magnesium Bimetallic Cooperation: A Mechanistic and Computational Study. ACS Catalysis 2020, 10, 7934–7944. (DOI: 10.1021/acscatal.0c01301) Zhao, H.; Xu, X.; Yu, H.; Li, B.; Xu, X.; Li, H.; Xu, L.; Fan, Q.; Walsh, P. J. Rh(I)-Catalyzed C6-Selective Decarbonylative Alkylation of 2-Pyridones with Alkyl Carboxylic Acids and Anhydrides. Org. Lett. 2020, 22, 4228-4234. (DOI: 10.1021/acs.orglett.0c01277) Liu, Z.; Li, M.; Deng, G.; Wei, W.; Feng, P.; Zi, Q.; Li, T.; Zhang, H.; Yang, X.; Walsh, P. J. Transition-metal-free C(sp3)–H/C(sp3)–H dehydrogenative coupling of saturated heterocycles with N-benzyl imines. Chem. Sci. 2020, 11, 7619-7625 (DOI: 10.1039/D0SC00031K) Caravan, R. L.; Vansco, M. F.; Au, K.; Khan, M. A. H.; Li, Y.-L.; Winiberg, F. A. F.; Zuraski, K.; Lin, Y.-H.; Chao, W.; Trongsiriwat, N.; Walsh, P. J.; Osborn, D. L.; Percival, C. J.; Lin, J. J.-M.; Shallcross, D. E.; Sheps, L.; Klippenstein, S. J.; Taatjes, C. A.; Lester, M. I. Direct kinetic measurements and theoretical predictions of an isoprene-derived Criegee intermediate. Proc. Natl. Acad. Sci. 2020, 201916711. (DOI: 10.1073/pnas.1916711117) Vansco, M. F.; Caravan, R. L.; Zuraski, K.; Winiberg, F. A. F.; Au, K.; Trongsiriwat, N.; Walsh, P. J.; Osborn, D. L.; Percival, C. J.; Khan, M. A. H.; Shallcross, D. E.; Taatjes, C. A.; Lester, M. I. Experimental Evidence of Dioxole Unimolecular Decay Pathway for Isoprene-Derived Criegee Intermediates. J. Phys. Chem. A 2020. (DOI: 10.1021/acs.jpca.0c02138) Guan, H.; Zhang, Q.; Walsh, P. J.; Mao, J. Nickel/Photoredox-Catalyzed Asymmetric Reductive Cross-Coupling of Racemic a-Chloro Esters with Aryl Iodides.Angew. Chem., Int. Ed., 2020, 59(13), 5172-5177, (DOI:10.1002/anie.201914175). Liang, Q.; Walsh, P. J.; Jia, T. Copper-Catalyzed Intermolecular Difunctionalization of Styrenes with Thiosulfonates and Arylboronic Acids via a Radical Relay Pathway. ACS Catalysis2019, 10, 2633-2639, (10.1021/acscatal.1029b04887). Zheng, Z.; Trofymchuk, O. S.; Kurogi, T.; Varela, E.; Mindiola, D. J.; Walsh, P. J. Selenenate Anions (PhSeO−) as Organocatalyst: Synthesis of trans-Stilbenes and a PPV Derivative. Adv. Syn. & Catal., 2020, 362, 659-666.(10.1002/adsc.201901201) Zhou, Y.; Wang, L.; Li, S.; Ma, S.; Walsh, P. J.; Bian, Q.; Li, F.; Wang, M.; Zhong, J. Enantioselective Addition of Alkynyl Esters and Ethers to Aldehydes Catalyzed by a Cyclopropyl Amino Alcohol Based Zinc Catalyst. Synlett2020, 31, 60-64. Yang, W.; Ling, B.; Hu, B.; Yin, H.; Mao, J.; Walsh, P. J. Synergistic N-Heterocyclic Carbene/Palladium-Catalyzed Umpolung 1,4-Addition of Aryl Iodides to Enals. Angew. Chem., Int. Ed., 2020, 59, 161-166. (DOI: 10.1002/anie.201912584) Guan, H.; Cao, X.; Walsh, P. J.; Mao, J. One-Pot Aminoalkylation of Aldehydes: Diastereoselective Synthesis of Vicinal Diamines with Azaarylmethylamines. Org. Lett.2019, 21, 8679-8683.(DOI: 10.1021/acs.orglett.9b03287) Ge, L.; Wang, D.-X.; Xing, R.; Ma, D.; Walsh, P. J.; Feng, C. Photoredox-catalyzed oxo-amination of aryl cyclopropanes. Nat. Commun.2019, 10, 4367 (DOI: 10.1038/s41467-019-12403-2) Liu, G.; Walsh, P. J.; Mao, J. Alkaline-Metal-Catalyzed One-Pot Aminobenzylation of Aldehydes with Toluenes. Org. Lett.2019, 21, 8514. (10.1021/acs.orglett.9b02737) Zhao, H.; Xu, X.; Luo, Z.; Cao, L.; Li, B.; Li, H.; Xu, L.; Fan, Q.; Walsh, P. J. Rhodium(i)-catalyzed C6-selective C–H alkenylation and polyenylation of 2-pyridones with alkenyl and conjugated polyenyl carboxylic acids. Chem. Sci.2019. 10, 10089 – 10096. (DOI: 10.1039/C9SC03672E) Vansco, M. F.; Marchetti, B.; Trongsiriwat, N.; Bhagde, T.; Wang, G.; Walsh, P. J.; Klippenstein, S. J.; Lester, M. I. Synthesis, electronic spectroscopy and photochemistry of methacrolein oxide: A four carbon unsaturated Criegee intermediate from isoprene ozonolysis. J. Am. Chem. Soc.2019141, 15058-15069. (doi.org/10.1021/jacs.9b05193) Yu, K.; Li, M.; Deng, G.; Liu, C.; Wang, J.; Liu, Z.; Zhang, H.; Yang, X.; Walsh, P. J. An Efficient Route to Isochromene Derivatives via Cascade Radical Cyclization and Radical-Radical Coupling. Adv. Syn. & Catal.2019, 361, 4354-4359 (doi:10.1002/adsc.201900497). Trongsiriwat, N.; Pu, Y.; Nieves-Quinones, Y.; Shelp, R. A.; Kozlowski, M. C.; Walsh, P. J. Reactions of 2-Aryl-1,3-Dithianes and [1.1.1]Propellane. Angew. Chem., Int. Ed.2019,58, 13416-13420, (doi:10.1002/anie.201905531). Wang, X.; Zeng, X.; Lin, Q.; Li, M.; Walsh, P. J.; Chruma, J. J. Palladium-Catalysed Decarboxylative Generation and Regiodivergent Prenylation of 2-Azaallyl Anions. Adv. Syn. & Catal.2019,361, 3751–37(DOI: 10.1002/adsc.201900491) Samant, S.; Huang, G.; Gao, G.; Zhang, Y.; Wolf, S.; Woods, C. N.; Jin, Y.; Walsh, P. J.; Fakhraai, Z. Exploring the Importance of Surface Diffusion in Stability of Vapor Deposited Organic Glasses. J. Phys. Chem. 2019, 123, 4108-4117 (DOI:10.1021/acs.jpcb.9b01012). Panetti, G. B.; Varela, E. J.; Gau, M. R.; Schelter, E. J.; Walsh, P. J. An investigation of the binding of (S)-monothioBINOLate to rare earth metal cations.Phosphorus, Sulfur, and Silicon and the Related Elements2019, 194,624-629. DIO:10.1080/10426507.2019.1602773 Moore, A. R.; Walsh, P.; Fakhraai, Z.; Riggleman, R. A. Effects of Microstructure Formation on the Stability of Vapor Deposited Glasses.PNAS2019,201821761 (doi: 10.1073/pnas.1821761116). Jiang, H.; Sha, S.-C.; Jeong, S. A.; Manor, B. C.; Walsh, P. J. Ni(NIXANTPHOS)-Catalyzed Mono-Arylation of Toluenes with Aryl Chlorides and Bromides.Org. Lett.2019,21, 1735–1739 (doi: 10.1021/acs.orglett.1029b00294). Wu, C.; Berritt, S.; Liang, X.; Walsh, P. J. Palladium-Catalyzed Enantioselective Alkenylation of Sulfenate Anions. Org. Lett. 2019,21, 960-964231. Deng, G.; Li, M.; Yu, K.; Liu, C.; Liu, Z.; Duan, S.; Chen, W.; Yang, X.; Zhang, H.; Walsh, P. J. Synthesis of Benzofuran Derivatives through Cascade Radical Cyclization/Intermolecular Coupling of 2-Azaallyls. Angew. Chem., Int. Ed.2019, 58, 2826-2830 Trongsiriwat, N.; Li, M.; Pascual-Escudero, A.; Yucel, B.; Walsh, P. J. Palladium-Catalyzed Allylic Alkylation of 2-Aryl-1,3-Dithianes, an Umpolung Synthesis of β,γ-Unsaturated Ketones. Adv. Syn. & Catal.2019, 361, 502-509 Wang, R.; Ma, M.; Gong, X.; Fan, X.; Walsh, P. J. Reductive Cross-Coupling of Aldehydes and Imines Mediated by Visible Light Photoredox Catalysis. Org. Lett.2019, 21, 27–31 (10.1021/acs.orglett.1028b03394). Duan, S.; Li, M.; Ma, X.; Chen, W.; Li, L.; Zhang, H.; Yang, X.; Walsh, P. J. Palladium-Catalyzed Alkenylation of Azaarylmethylamines with Vinyl Halides. Adv. Syn. & Catal.2018,360, 4837-4842 Wang, H.; Chen, S.; Liu, G.; Guan, H.; Zhong, D.; Cai, J.; Zheng, Z.; Mao, J.; Walsh, P. J. Synthesis of Diaryl Selenides via Palladium-Catalyzed Debenzylative Cross-Coupling of Aryl Benzyl Selenides with Aryl Bromides. Organometallics2018, 37, 4086-4091226. Fan,X.; Gong,X. Ma, M.; Wang,R. Walsh, P. J. Visible Light-Promoted CO2Fixation with Imines: Synthesis of Diaryl α-Amino Acids. Nat. Commun.2018, 9, 4936 Shelp, R. A.; Walsh, P. J. Synthesis of BCP Benzylamines From 2-Azaallyl Anions and [1.1.1]Propellane. Angew. Chem., Int. Ed.2018, 57, 15857-15861224. Liang, X.; Wu, C.; Zheng, Z.; Walsh, P. J. Nickel-Catalyzed Oxidative Coupling Reaction of Phenyl Benzyl Sulfoxides. Organometallics2018, 37, 3132–3141223. Sha, S.-C.; Tcyrulnikov, S.; Li, M.; Hu, B.; Fu, Y.; Kozlowski, M. C.; Walsh, P. J. Cation-pInteractions in the Benzylic Arylation of Toluenes with Bimetallic Catalysts. J. Am. Chem. Soc. 2018,40, 12415-12423 (10.1021/jacs.8b05143). Wang, Q.; Poznik, M.; Li, M.; Walsh, P. J.; Chruma, J. J. 2-Azaallyl anions as light-tunable super-electron-donors: transition-metal-free coupling with aryl halides. Adv. Syn. & Catal.2018, 360, 2854-2868219. Jiang, H.; Bellomo, A.; Zhang, M.; Carroll, P. J.; Manor, B. C.; Jia, T.; Walsh, P. J. Palladium-Catalyzed Direct C–H Arylation of 3-(Methylsulfinyl)thiophenes. Org. Lett.2018, 20, 2522-2525218. Wang, R.; Ma, M.; Gong, X.; Panetti, G. B.; Fan, X.; Walsh, P. J. Visible-Light-Mediated Umpolung Reactivity of Imines: Ketimine Reductions with Cy2NMe and Water. Org. Lett.2018, 20, 2433–2436217. Liu, Z.-F.; Li, M.; Wang, B.; Deng, G.; Chen, W.; Kim, B.-S.; Zhang, H.; Yang, X.-D.; Walsh, P. Chemoselective synthesis of aryl(pyridinyl)methanol derivatives through Ni-NIXANTPHOS catalyzed a-arylation and tandem arylation/rearrangement of pyridylmethyl ethers. Org. Chem. Front.2018, 5, 1870-1876216. Zhang, S.; Hu, B.; Zheng, Z.; Walsh, P. J. Palladium-Catalyzed Triarylation of sp3C−H Bonds in Heteroarylmethanes: Synthesis of Triaryl(heteroaryl)methanes. Adv. Syn. & Catal.2018,360,1493– 1498 Kim, B.-S.; Gutierrez, O.; Kozlowski, M. C.; Walsh, P. J. A Simple Procedure for the Synthesis of β-Hydroxyallenamides via Homoallenylation of Aldehydes. Adv. Synth. Catal.2018, 360(7), 1426–1432. Mao, J.; Zhang, J.; Zhang, S.; Walsh, P. J. NIXANTPHOS: A Highly Active Ligand for Palladium-Catalyzed Buchwald–Hartwig Amination of Unactivated Aryl Chlorides. Dalt. Trans.2018, 47(26), 8690–8696.213 Li, M.; Berritt, S.; Wang, C.; Yang, X.; Liu, Y.; Sha, S.-C.; Wang, B.; Wang, R.; Gao, X.; Li, Z.; et al. Sulfenate Anions as Organocatalysts for Benzylic Chloromethyl Coupling Polymerization via C=C Bond Formation. Nat. Commun.2018, 9(1), 1754.212. Li, J.; Wu, C.; Zhou, B.; Walsh, P. J. Nickel-Catalyzed C(Sp3)–H Arylation of Diarylmethane Derivatives with Aryl Fluorides. J. Org. Chem.2018, 83(5), 2993–2999 Wang, Z.; Zheng, Z.; Xu, X.; Mao, J.; Walsh, P. J. One-Pot Aminobenzylation of Aldehydes with Toluenes. Nat. Commun.2018, 9(1), 3365. Lin, T.; Mi, J.; Song, L.; Gan, J.; Luo, P.; Mao, J.; Walsh, P. J. Nickel-Catalyzed Desymmetrizing Cross-Electrophile Coupling of Cyclic Meso-Anhydrides. Org. Lett.2018, 20(4), 1191–1194. Liu, F.; Zhong, J.; Zhou, Y.; Gao, Z.; Walsh, P. J.; Wang, X.; Ma, S.; Hou, S.; Liu, S.; Wang, M.; et al. Cobalt-Catalyzed Enantioselective Negishi Cross-Coupling of Racemic α-Bromo Esters with Arylzincs. Chem. – A Eur. J. 2018, 24(9), 2059–2064.