Peng Liu Research Group
Computational Organic Chemistry
Department of Chemistry
University of Pittsburgh
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Publications @ Pitt

All Publications
By Research Areas
  • C–H and C–C Functionalization
  • Olefin Functionalization
  • Stereoselective Catalysis 
  • Polymerization
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94. C–H Functionalization | C(alkenyl)–H Activation via Six-Membered Palladacycles: Catalytic 1,3-Diene Synthesis​

Mingyu Liu, Pusu Yang, Malkanthi K. Karunananda, Yanyan Wang, Peng Liu*, and Keary M. Engle*
​
J. Am. Chem. Soc., in press, DOI: 10.1021/jacs.8b02124. (PDF)

92. C–H Functionalization | ​A General Strategy for Synthesis of Cyclophane-braced Peptide Macrocycles via Palladium-Catalysed Intramolecular sp3 C−H Arylation

Xuekai Zhang, Gang Lu, Meng Sun, Madhu Mahankali, Yanfei Ma, Mingming Zhang, Wangde Hua, Yuting Hu, Qingbing Wang, Jinghuo Chen, Gang He*, Xiangbing Qi*, Weijun Shen*, Peng Liu*, and Gong Chen*
​​
Nature. Chem., in press, DOI: 10.1038/s41557-018-0006-y. (PDF)

89. C–H Functionalization | Catalytic C−H Trifluoromethoxylation of Arenes and Heteroarenes​
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Weijia Zheng, Cristian A. Morales‐Rivera, Johnny W. Lee, Peng Liu*, and Ming‐Yu Ngai*
​​
Angew. Chem. Int. Ed., in press, DOI: 10.1002/ange.201800598​. (PDF)

87. C–H Functionalization | Predictive Model for Oxidative C−H Bond Functionalization Reactivity with 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)​
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Cristian A. Morales-Rivera, Paul E. Floreancig*, and Peng Liu*
​​
J. Am. Chem. Soc., in press, DOI: 10.1021/jacs.7b08902. (PDF)
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85. C–H Functionalization | Experimental and Computational Exploration of Para-Selective Silylation Involving H-Bonded Template
​​

Arun Maji, Srimanta Guin, Sheng Feng, Amit Dahiya, Vikas Kumar Singh, Peng Liu*, and Debabrata Maiti*
​​
Angew. Chem. Int. Ed., in press, DOI: 10.1002/anie.201708449. (PDF)

82. C–H Functionalization | ​A Unified Photoredox-Catalysis Strategy for C(sp3)−H Hydroxylation and Amidation Using Hypervalent Iodine
​​
Guo-Xing Li, Cristian A. Morales-Rivera, Fang Gao, Yaxin Wang, Gang He, Peng Liu*, and Gong Chen*
​
Chem. Sci., accepted, DOI: 10.1039/C7SC02773G. (PDF)

81. C–H Functionalization | Intramolecular C−H Activation Reactions of Ru(NHC) Complexes Combined with H2 Transfer to Alkenes: A Theoretical Elucidation of Mechanisms and Effects of Ligands on Reactivities​
​​
Katharina Marie Wenz, Peng Liu*, and K. N. Houk*
​
Organometallics, accepted, DOI: 10.1021/acs.organomet.7b00531. (PDF)

78. C–H Functionalization | Computational Study of Ni-Catalyzed C−H Functionalization: Factors that Control the Competition of Oxidative Addition and Radical Pathways​
​​
Humair M. Omer and Peng Liu*

J. Am. Chem. Soc., 2017, 139, 9909–9920. (PDF)
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69. C–C Functionalization | Catalytic Activation of Carbon–Carbon Bonds in Cyclopentanones
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Ying Xia, Gang Lu, Peng Liu*, and Guangbin Dong*
​
Nature, 2016, 539, 546–550. (PDF)
  • News coverage: C&EN and PQI.
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68. C–H Functionalization | Benzazetidine Synthesis via Palladium-Catalyzed Intramolecular C−H Amination
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Gang He*, Gang Lu, Zhengwei Guo, Peng Liu*, and Gong Chen*
​
Nature Chem., 2016, 8, 1131–1136. (PDF)
  • Highlighted in Synfacts. News coverage: Phys.org.
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67. Metal-Free C–​H Functionalization | Photoredox-Mediated Minisci C−H Alkylation of N-Heteroarenes Using Boronic Acids and Hypervalent Iodine​
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Guo-Xing Li, Cristian A. Morales-Rivera, Yaxin Wang, Fang Gao, Gang He, Peng Liu*, and Gong Chen*
​​
Chem. Sci., 2016, 7, 6407–6412. (PDF)

64. Metal-Free C–​H Functionalization | Mechanistic Studies on Intramolecular C–H Trifluoromethoxylation of (Hetero)arenes via OCF3-Migration​
​​
Katarzyna N. Hojczyk, Zhen Lei, Cristian A. Morales-Rivera, Peng Liu, and Ming-Yu Ngai*
​
Org. Biomol. Chem., 2016, 14, 5599–5605​. (PDF)

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57. C–C Activation | Computational Study of Rh-Catalyzed Carboacylation of Olefins: Ligand-Promoted Rhodacycle Isomerization Enables Regioselective C–C Bond Functionalization of Benzocyclobutenones

Gang Lu, Cheng Fang, Tao Xu, Guangbin Dong, and Peng Liu*

J. Am. Chem. Soc., 2015, 137, 8274–8283. (PDF)

The mechanism, reactivity, regio- and enantioselectivity of the Rh-catalyzed carboacylation of benzocyclobutenones are investigated using DFT calculations. The calculations indicate that the selective activation of the relatively unreactive C1–C2 bond in benzocyclobutenone is achieved via initial C1–C8 bond oxidative addition, followed by rhodacycle isomerization via decarbonylation and CO insertion. (Full abstract)


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55. C–H Functionalization | Mechanism and Origins of Selectivities in the Copper-Catalyzed Dearomatization-Induced ortho C–H Cyanation of Vinylarenes 

Yang Yang and Peng Liu* 

ACS. Catal., 2015, 5, 2944–2951. (PDF)

DFT calculations indicated this C–H cyanation is composed of two discrete catalytic cycles (the copper-catalyzed electrophilic cyanative dearomatization and the subsequent base-catalyzed hydrogen transposition) that furnish the ortho C–H cyanated arenes. (Full abstract) 
  • Highlighted in the ACS Select Virtual Issue on First Row Transition Metal Complexes.

86. Olefin Functionalization | Ligand–Substrate Dispersion Facilitates the Copper-Catalyzed Hydroamination of Unactivated Olefins
​​

Gang Lu, Richard Y. Liu, Yang Yang, Cheng Fang, Daniel S. Lambrecht*, Stephen L. Buchwald*, and Peng Liu*
​​
J. Am. Chem. Soc., in press, DOI: 10.1021/jacs.7b07373. (PDF)
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84. Olefin Functionalization | Tridentate Directing Groups Stabilize 6-Membered Palladacycles in Catalytic Alkene Hydrofunctionalization
​​

Miriam L. O’Duill, Rei Matsuura, Yanyan Wang, Joshua L. Turnbull, John A. Gurak Jr., De-Wei Gao, Gang Lu, Peng Liu*, and Keary M. Engle*
​
J. Am. Chem. Soc., 2017, 139, 15576–15579. (PDF)

79. Catalytic Intermolecular Carboamination of Unactivated Alkenes via Directed Aminopalladation​
​​
Zhen Liu, Yanyan Wang, Zichen Wang, Tian Zeng, Peng Liu*, and Keary M. Engle*
​
J. Am. Chem. Soc., 2017, 139, 11261–11270. (PDF)

75. Rhodium-Catalyzed Enantioselective Radical Addition of CX4 Reagents to Olefins​​
​​
Bo Chen, Cheng Fang, Peng Liu*, and Joseph M. Ready*
​
Angew. Chem. Int. Ed., 2017, 56, 8780–8784. (PDF)

66. Copper-Catalyzed Asymmetric Addition of Olefin-Derived Nucleophiles to Ketones​
​​
Yang Yang, Ian B. Perry, Gang Lu, Peng Liu*, and Stephen L. Buchwald*
​
Science, 2016, 353, 144–150. (PDF)
  • Highlighted in C&EN and Synfacts.

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61. Mechanism and Origins of Ligand-Controlled Linear versus Branched Selectivity of Iridium-Catalyzed Hydroarylation of Alkenes
​​
Genping Huang* and Peng Liu*
​
ACS Catal., 2016, 6, 809–820. (PDF)


58. Catalytic Asymmetric Hydroamination of Unactivated Internal Olefins to Aliphatic Amines

Yang Yang, Shi-Liang Shi, Dawen Niu, Peng Liu, and Stephen L. Buchwald*

Science, 2015, 349, 62–66. (PDF)

Catalytic assembly of enantiopure aliphatic amines from abundant and readily available precursors has long been recognized as a paramount challenge in synthetic chemistry. Here, we describe a mild and general copper-catalyzed hydroamination that effectively converts unactivated internal olefins—an important yet unexploited class of abundant feedstock chemicals—into highly enantioenriched α-branched amines (≥96% enantiomeric excess) featuring two minimally differentiated aliphatic substituents. (Full abstract)
  • Highlighted in C&EN and Chemistry World.
83. Asymmetric Catalysis | Computationally Guided Catalyst Design in the Type I Dynamic Kinetic Asymmetric Pauson–Khand Reaction of Allenyl Acetates
​​
Lauren C. Burrows, Luke T. Jesikiewicz, Gang Lu , Steven J. Geib, Peng Liu* , and Kay M. Brummond*
​
J. Am. Chem. Soc., 2017, 139, 15022–15032. (PDF)

77. Asymmetric Reductive Coupling | NHC Ligands Tailored for Simultaneous Regio- and Enantiocontrol in Nickel-Catalyzed Reductive Couplings​
​​
Hengbin Wang, Gang Lu, Grant J. Sormunen, Hasnain A. Malik, Peng Liu,* and John Montgomery*
​
J. Am. Chem. Soc., 2017, 139, 9317–9324. (PDF)

75. Atom Transfer Radical Addition | Rhodium-Catalyzed Enantioselective Radical Addition of CX4 Reagents to Olefins​​
​​
Bo Chen, Cheng Fang, Peng Liu*, and Joseph M. Ready*
​
Angew. Chem. Int. Ed., accepted, DOI: 10.1002/anie.201704074. (PDF)

73. Carbohydrate Functionalization | Catalytic Site-selective Acylation of Carbohydrates Directed by Cation-n Interaction​
​​
Guozhi Xiao, Gabriel A. Cintron-Rosado, Daniel A. Glazier, Baomin Xi, Can Liu, Peng Liu*, and Weiping Tang*
​
J. Am. Chem. Soc., 2017, 139, 4346–4349. (PDF)
  • Highlighted in JACS Spotlights.​

66. Olefin Hydrofunctionalization | Copper-Catalyzed Asymmetric Addition of Olefin-Derived Nucleophiles to Ketones​
​​
Yang Yang, Ian B. Perry, Gang Lu, Peng Liu*, and Stephen L. Buchwald*
​
Science, 2016, 353, 144–150. (PDF)
  • Highlighted in C&EN and Synfacts.

58. Olefin Hydrofunctionalization | Catalytic Asymmetric Hydroamination of Unactivated Internal Olefins to Aliphatic Amines

Yang Yang, Shi-Liang Shi, Dawen Niu, Peng Liu, and Stephen L. Buchwald*

Science, 2015, 349, 62–66. (PDF)

Catalytic assembly of enantiopure aliphatic amines from abundant and readily available precursors has long been recognized as a paramount challenge in synthetic chemistry. Here, we describe a mild and general copper-catalyzed hydroamination that effectively converts unactivated internal olefins—an important yet unexploited class of abundant feedstock chemicals—into highly enantioenriched α-branched amines (≥96% enantiomeric excess) featuring two minimally differentiated aliphatic substituents. (Full abstract)
  • Highlighted in C&EN and Chemistry World.
80. Polymerization | The Origins of the Stereoretentive Mechanism of Olefin Metathesis with Ru-Dithiolate Catalysts​
​​
Jessica M. Grandner, Huiling Shao, Robert H. Grubbs, Peng Liu*, and K. N. Houk*
​
J. Org. Chem., accepted, DOI: 10.1021/acs.joc.7b02129. (PDF)

71. Multi-Tasking Catalysis | A Photoswitchable Olefin Metathesis Catalyst
​​
Aaron J. Teator, Huiling Shao, Gang Lu, Peng Liu*, and Christopher W. Bielawski*
​
Organometallics, 2017, 36, 490–497. (PDF)

70. Multi-Tasking Catalysis | A Ring-Opening Metathesis Polymerization Catalyst That Exhibits Redox-Switchable Monomer Selectivities
​​

Dominika N. Lastovickova, Huiling Shao, Gang Lu, Peng Liu*, and Christopher W. Bielawski*
​
Chem. Eur. J., 2017, 23, 5994–6000. (PDF)

62. Metal-Free ATRP | Mechanism of Photoinduced Metal-Free Atom Transfer Radical Polymerization: Experimental and Computational Studies​
​​
Xiangcheng Pan, Cheng Fang, Marco Fantin, Nikhil Malhotra , Woong Young So, Linda A. Peteanu, Abdirisak A. Isse, Armando Gennaro,* Peng Liu,* and Krzysztof Matyjaszewski*
​
J. Am. Chem. Soc., 2016, 138, 2411–2425. (PDF)
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