Eric M. Simmons

Bristol-Myers Squibb (United States)

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Steven R. Wisniewski

Bristol-Myers Squibb (United States)

Paul J. Chirik

Princeton University

L. Reginald Mills

Princeton University

Junho Kim

Princeton University

David Gygi

Harvard University

Richmond Sarpong

University of California, Berkeley

Jason M. Stevens

Bristol-Myers Squibb (United States)

Martin D. Eastgate

Bristol-Myers Squibb (United States)

Albert J. DelMonte

Bristol-Myers Squibb (United States)

Antonio Ramı́rez

Bristol-Myers Squibb (United States)

Cooperative Institutions

Bristol-Myers Squibb (United States)

186

Bristol-Myers Squibb (Germany)

The Bristol-Myers Squibb Children's Hospital

Princeton University

Biocon (India)

Bristol-Myers Squibb (India)

Merck & Co., Inc., Rahway, NJ, USA (United States)

University of California, Berkeley

Scripps Research Institute

Bristol-Myers Squibb (United Kingdom)

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Iridium-Catalyzed Arene Ortho-Silylation by Formal Hydroxyl-Directed C−H Activation

Journal of the American Chemical Society (2010)

Eric M. Simmons John F. Hartwig

A strategy for the ortho-silylation of aryl ketone, benzaldehyde, and benzyl alcohol derivatives has been developed in which a hydroxyl group formally serves as the directing element for Ir-catalyzed arene C−H bond activation. One-pot generation of a (hydrido)silyl ether from the carbonyl compound or alcohol is followed by dehydrogenative cyclization at 80−100 °C in the presence of norbornene as a hydrogen acceptor and the combination of 1 mol % [Ir(cod)OMe]2 and 1,10-phenanthroline as a catalyst to form benzoxasiloles. The synthetic utility of the benzoxasilole products is demonstrated by conversion to phenol or biaryl derivatives by Tamao−Fleming oxidation or Hiyama cross-coupling. Both of these transformations of the C−H silylation products exploit the Si−O bond in the system and proceed by activation of the silyl moiety with hydroxide, rather than fluoride.

Moiety

Silyl ether

Benzaldehyde

10.1021/ja1086547

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Citations (235)

CCDC 2110300: Experimental Crystal Structure Determination

The Cambridge Structural Database (2023)

L. Reginald Mills David Gygi Jacob Ryan Ludwig Eric M. Simmons Steven R. Wisniewski

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccdc.csd.cc28ty68

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Citations (0)

Synthetic Strategies Directed Towards the Cortistatin Family of Natural Products

European Journal of Organic Chemistry (2010)

Alison R. H. Narayan Eric M. Simmons Richmond Sarpong

Abstract Since their isolation by Kobayashi and co‐workers, the cortistatins have captured the attention both of the synthetic chemistry community and of researchers interested in exploiting the potent anti‐angiogenic activity of these natural products. The unique rearranged steroidal cortistatin core has become the target of numerous synthetic efforts, which are detailed herein.

10.1002/ejoc.201000247

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Citations (50)

Unlocking Tertiary Acids for Metallaphotoredox C(sp2)-C(sp3) Decarboxylative Cross-Couplings

Junqing Guo Derek Norris Antonio Ramı́rez Jack L. Sloane Eric M. Simmons

Dual nickel photoredox catalysis conditions have been developed for the decarboxylative cross-coupling of aryl halides and carboxylic acids containing fully substituted alpha carbons, a valuable but challenging substrate class for C(sp2)–C(sp3) bond-forming reactions. High-throughput experimentation identified Ni(TMHD)2 as the optimal precatalyst for this reaction in contrast to the nickel-bipyridyl complexes typically employed in decarboxylative couplings, which predominantly furnished undesired C–O products. Computational work provides insight into the potential mechanistic underpinnings for the C–C vs. C–O selectivity for the nickel-diketonate complex.

Decarboxylation

10.26434/chemrxiv-2023-tbvsv

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Citations (3)

High-Throughput Automation in Chemical Process Development

Annual Review of Chemical and Biomolecular Engineering (2017)

Joshua A. Selekman Jun Qiu Kristy Tran Jason M. Stevens Victor W. Rosso

High-throughput (HT) techniques built upon laboratory automation technology and coupled to statistical experimental design and parallel experimentation have enabled the acceleration of chemical process development across multiple industries. HT technologies are often applied to interrogate wide, often multidimensional experimental spaces to inform the design and optimization of any number of unit operations that chemical engineers use in process development. In this review, we outline the evolution of HT technology and provide a comprehensive overview of how HT automation is used throughout different industries, with a particular focus on chemical and pharmaceutical process development. In addition, we highlight the common strategies of how HT automation is incorporated into routine development activities to maximize its impact in various academic and industrial settings.

Laboratory automation

Process development

10.1146/annurev-chembioeng-060816-101411

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Citations (108)

CCDC 2210685: Experimental Crystal Structure Determination

The Cambridge Structural Database (2022)

Cong Bi James Chadwick Merrill L. Davies Albert J. DelMonte Peng Geng

10.5517/ccdc.csd.cc2d6dfg

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Design and evolution of the BMS process greenness scorecard

Green Chemistry (2017)

David K. Leahy Eric M. Simmons Víctor Hung Jason T. Sweeney William F. Fleming

A process greenness scorecard has been developed that provides a comprehensive assessment of greenness aspects not encompassed by mass-based metrics, including environmental, health and safety impacts, in order to facilitate the design of greener, more benign and inherently safer processes.

SAFER

10.1039/c7gc02190a

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Citations (20)

CCDC 2260987: Experimental Crystal Structure Determination

The Cambridge Structural Database (2023)

L. Reginald Mills Francesca Di Mare David Gygi Heejun Lee Eric M. Simmons

10.5517/ccdc.csd.cc2fwr25

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Citations (0)

CCDC 2260991: Experimental Crystal Structure Determination

The Cambridge Structural Database (2023)