Brett R. Ambler

The University of Texas at Austin

Author Statistics

Papers

Citation

H-Index

i-10 index

Research Trends

Author Order

Document Type

Co-Authors

Ryan A. Altman

Purdue University West Lafayette

Michael J. Krische

The University of Texas at Austin

Ben W. H. Turnbull

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

Matthias Bender

The University of Texas at Austin

Santosh Peddi

LAC+USC Medical Center

Lingui Zhu

Shanghai Institute of Organic Chemistry

Thomas Wurm

Heidelberg University

Nancy O. Huynh

The University of Texas at Austin

Sankar Rao Suravarapu

The University of Texas at Austin

Maulen M. Uteuliyev

The University of Texas at Austin

Cooperative Institutions

University of Kansas

The University of Texas at Austin

The University of Texas at San Antonio

Johns Hopkins University

Chinese Academy of Sciences

University of Southern California

Heidelberg University

Seoul National University

Robert Bosch (Germany)

University of California, Irvine

Author Statistics

Papers

Citation

H-Index

i-10 index

Research Field

Decarboxylative Fluorination Strategies for Accessing Medicinally- Relevant Products

Current Topics in Medicinal Chemistry (2014)

Yupu Qiao Lingui Zhu Brett R. Ambler Ryan A. Altman

Fluorinated organic compounds have a long history in medicinal chemistry, and synthetic methods to access target fluorinated compounds are undergoing a revolution. One powerful strategy for the installation of fluorinecontaining functional groups includes decarboxylative reactions. Benefits of decarboxylative approaches potentially include: 1) readily available substrates or reagents 2) mild reaction conditions; 3) simplified purification. This focus review highlights the applications of decarboxylation strategies for fluorination reactions to access compounds with biomedical potential. The manuscript highlights on two general strategies, fluorination by decarboxylative reagents and by decarboxylation of substrates. Where relevant, examples of medicinally useful compounds that can be accessed using these strategies are highlighted.

Decarboxylation

Trifluoromethylation

10.2174/1568026614666140202210850

Cite

Citations (22)

Copper-Catalyzed Decarboxylative Trifluoromethylation of Allylic Bromodifluoroacetates

Organic Letters (2013)

Brett R. Ambler Ryan A. Altman

The development of new synthetic fluorination reactions has important implications in medicinal, agricultural, and materials chemistries. Given the prevalence and accessibility of alcohols, methods to convert alcohols to trifluoromethanes are desirable. However, this transformation typically requires four-step processes, specialty chemicals, and/or stoichiometric metals to access the trifluoromethyl-containing product. A two-step copper-catalyzed decarboxylative protocol for converting allylic alcohols to trifluoromethanes is reported. Preliminary mechanistic studies distinguish this reaction from previously reported Cu-mediated reactions.

Trifluoromethylation

Stoichiometry

10.1021/ol402780k

Cite

Citations (47)

CCDC 1562342: Experimental Crystal Structure Determination

The Cambridge Structural Database (2017)

Matthias Bender Ben W. H. Turnbull Brett R. Ambler Michael J. Krische

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.cc1pfr40

Cite

Citations (0)

ChemInform Abstract: Ligand‐Controlled Regioselective Copper‐Catalyzed Trifluoromethylation to Generate (Trifluoromethyl)allenes.

ChemInform (2015)

Brett R. Ambler Santosh Peddi Ryan A. Altman

Abstract The ability of bipyridyl‐derived ligands to control the regioselectivity of Cu‐catalyzed nucleophilic trifluoromethylation reactions of propargyl electrophiles to generate (trifluoromethyl)allenes is demonstrated for the first time.

Trifluoromethylation

10.1002/chin.201538076

Cite

Citations (0)

Copper-Catalyzed Decarboxylative Trifluoromethylation Reactions

Brett R. Ambler

Trifluoromethylation

Source

Cite

Citations (0)

CCDC 1562340: Experimental Crystal Structure Determination

The Cambridge Structural Database (2017)

Matthias Bender Ben W. H. Turnbull Brett R. Ambler Michael J. Krische

10.5517/ccdc.csd.cc1pfr2y

Cite

Citations (0)

Catalytic One-Step Deoxytrifluoromethylation of Alcohols

The Journal of Organic Chemistry (2019)

Francisco de Azambuja Sydney M. Lovrien Patrick Ross Brett R. Ambler Ryan A. Altman

A new bench-stable trifluoromethylation reagent, phenyl bromodifluoroacetate, converts readily available alcohols to trifluoromethanes in a Cu-catalyzed deoxytrifluoromethylation reaction. This reaction streamlines access to target biologically active molecules, and should be useful for a variety of medicinal, agricultural, and materials chemists.

Trifluoromethylation

10.1021/acs.joc.8b03072

Cite

Citations (13)

Copper-Catalyzed Synthesis of Trifluoroethylarenes from Benzylic Bromodifluoroacetates

The Journal of Organic Chemistry (2015)

Brett R. Ambler Lingui Zhu Ryan A. Altman

Trifluoroethylarenes are found in a variety of biologically active molecules, and strategies for accessing this substructure are important for developing therapeutic candidates and biological probes. Trifluoroethylarenes can be directly accessed via nucleophilic trifluoromethylation of benzylic electrophiles; however, current catalytic methods do not effectively transform electron-deficient substrates and heterocycles. To address this gap, we report a Cu-catalyzed decarboxylative trifluoromethylation of benzylic bromodifluoroacetates. To account for the tolerance of sensitive functional groups, we propose an inner-sphere mechanism of decarboxylation.

Trifluoromethylation

Decarboxylation

10.1021/acs.joc.5b01343

Cite

Citations (23)

CCDC 1562341: Experimental Crystal Structure Determination

The Cambridge Structural Database (2017)

Matthias Bender Ben W. H. Turnbull Brett R. Ambler Michael J. Krische

10.5517/ccdc.csd.cc1pfr3z

Cite

Citations (0)

CCDC 1845201: Experimental Crystal Structure Determination

The Cambridge Structural Database (2018)

Brett R. Ambler Ben W. H. Turnbull Sankar Rao Suravarapu Maulen M. Uteuliyev Nancy O. Huynh

10.5517/ccdc.csd.cc1zy2mm

Cite

Citations (0)