Conor E. Brigham

University of Michigan–Ann Arbor

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i-10 index

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Co-Authors

Melanie S. Sanford

University of Michigan–Ann Arbor

Christian A. Malapit

Northwestern University

Naish Lalloo

University of Michigan–Ann Arbor

Margarida Borrell

University of Girona

Michael W. Milbauer

University of Michigan–Ann Arbor

James R. Bour

Wayne State University

S. Maryamdokht Taimoory

University of Michigan–Ann Arbor

Alexander Bunnell

University of Michigan–Ann Arbor

ChristianA. Malapit

Cooperative Institutions

University of Michigan–Ann Arbor

University of Girona

Argonne National Laboratory

Ann Arbor Center for Independent Living

Nantes Université

RWTH Aachen University

University of Basel

University of Cambridge

Toyohashi University of Technology

Normandie Université

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CCDC 1837039: Experimental Crystal Structure Determination

The Cambridge Structural Database (2018)

Christian A. Malapit James R. Bour Conor E. Brigham Melanie S. Sanford

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.cc1znlbk

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Palladium-Catalyzed Decarbonylative Coupling of (Hetero)Aryl Boronate Esters with Difluorobenzyl Glutarimides

Organic Letters (2023)

Alexander Bunnell Naish Lalloo Conor E. Brigham Melanie S. Sanford

This report describes the Pd-catalyzed decarbonylative coupling of difluorobenzyl glutarimides with (hetero)aryl boronate esters to yield difluorobenzyl-substituted (hetero)arene products. The use of PAd2Bu as the phosphine ligand in combination with neopentylboronate ester nucleophiles proved critical for the selective formation of the decarbonylative coupling product versus analogous difluorobenzyl ketone. This transformation is effective for electronically diverse (hetero)aryl boronate esters and substituted difluorobenzyl glutarimides.

Decarbonylation

10.1021/acs.orglett.3c03071

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Correction to “Mechanism-Driven Development of Group 10 Metal-Catalyzed Decarbonylative Coupling Reactions”

Accounts of Chemical Research (2023)

Naish Lalloo Conor E. Brigham Melanie S. Sanford

ADVERTISEMENT RETURN TO ISSUEPREVAddition/CorrectionNEXTORIGINAL ARTICLEThis notice is a correctionCorrection to “Mechanism-Driven Development of Group 10 Metal-Catalyzed Decarbonylative Coupling Reactions”Naish LallooNaish LallooMore by Naish Lalloohttps://orcid.org/0000-0001-9926-0387, Conor E. BrighamConor E. BrighamMore by Conor E. Brigham, and Melanie S. SanfordMelanie S. SanfordMore by Melanie S. Sanfordhttps://orcid.org/0000-0001-9342-9436Cite this: Acc. Chem. Res. 2023, 56, 12, 1683Publication Date (Web):May 25, 2023Publication History Received11 May 2023Published online25 May 2023Published inissue 20 June 2023https://doi.org/10.1021/acs.accounts.3c00277Copyright © 2023 American Chemical SocietyRIGHTS & PERMISSIONSArticle Views633Altmetric-Citations-LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (728 KB) Get e-Alertsclose Get e-Alerts

10.1021/acs.accounts.3c00277

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CCDC 2099725: Experimental Crystal Structure Determination

The Cambridge Structural Database (2021)

Naish Lalloo Christian A. Malapit S. Maryamdokht Taimoory Conor E. Brigham Melanie S. Sanford

10.5517/ccdc.csd.cc28gy2s

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Nickel-Catalyzed Decarbonylative Synthesis of Fluoroalkyl Thioethers

ACS Catalysis (2020)

Conor E. Brigham Christian A. Malapit Naish Lalloo Melanie S. Sanford

This report describes the development of a nickel-catalyzed decarbonylative reaction for the synthesis of fluoroalkyl thioethers (RFSR) from the corresponding thioesters. Readily available, inexpensive, and stable fluoroalkyl carboxylic acids (RFCO2H) serve as the fluoroalkyl (RF) source in this transformation. Stoichiometric organometallic studies reveal that RF–S bond-forming reductive elimination is a challenging step in the catalytic cycle. This led to the identification of diphenylphosphinoferrocene as the optimal ligand for this transformation. Ultimately, this method was applied to the construction of diverse fluoroalkyl thioethers (RFSR), with R = both aryl and alkyl.

Stoichiometry

Catalytic cycle

Reductive elimination

10.1021/acscatal.0c02950

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Citations (55)

Nickel-Catalyzed Decarbonylative Amination of Carboxylic Acid Esters

Journal of the American Chemical Society (2020)

Christian A. Malapit Margarida Borrell Michael W. Milbauer Conor E. Brigham Melanie S. Sanford

The reaction of carboxylic acid derivatives with amines to form amide bonds has been the most widely used transformation in organic synthesis over the past century. Its utility is driven by the broad availability of the starting materials as well as the kinetic and thermodynamic driving force for amide bond formation. As such, the invention of new reactions between carboxylic acid derivatives and amines that strategically deviate from amide bond formation remains both a challenge and an opportunity for synthetic chemists. This report describes the development of a nickel-catalyzed decarbonylative reaction that couples (hetero)aromatic esters with a broad scope of amines to form (hetero)aryl amine products. The successful realization of this transformation was predicated on strategic design of the cross-coupling partners (phenol esters and silyl amines) to preclude conventional reactivity that forms inert amide byproducts.

Amide

Reactivity

Peptide bond

10.1021/jacs.9b13531

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Citations (60)

CCDC 1837038: Experimental Crystal Structure Determination

The Cambridge Structural Database (2018)

Christian A. Malapit James R. Bour Conor E. Brigham Melanie S. Sanford

10.5517/ccdc.csd.cc1znl9j

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Nickel-CatalyzedDecarbonylative Amination of CarboxylicAcid Esters

Figshare (2020)

ChristianA. Malapit Margarida Borrell Michael W. Milbauer Conor E. Brigham Melanie S. Sanford

Amide

Reactivity

Peptide bond

Organic Synthesis

10.1021/jacs.9b13531.s003

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Decarbonylative Fluoroalkylation at Palladium(II): From Fundamental Organometallic Studies to Catalysis

Journal of the American Chemical Society (2021)

Naish Lalloo Christian A. Malapit S. Maryamdokht Taimoory Conor E. Brigham Melanie S. Sanford

This Article describes the development of a decarbonylative Pd-catalyzed aryl–fluoroalkyl bond-forming reaction that couples fluoroalkylcarboxylic acid-derived electrophiles [RFC(O)X] with aryl organometallics (Ar–M′). This reaction was optimized by interrogating the individual steps of the catalytic cycle (oxidative addition, carbonyl de-insertion, transmetalation, and reductive elimination) to identify a compatible pair of coupling partners and an appropriate Pd catalyst. These stoichiometric organometallic studies revealed several critical elements for reaction design. First, uncatalyzed background reactions between RFC(O)X and Ar–M′ can be avoided by using M′ = boronate ester. Second, carbonyl de-insertion and Ar–RF reductive elimination are the two slowest steps of the catalytic cycle when RF = CF3. Both steps are dramatically accelerated upon changing to RF = CHF2. Computational studies reveal that a favorable F2C–H---X interaction contributes to accelerating carbonyl de-insertion in this system. Finally, transmetalation is slow with X = difluoroacetate but fast with X = F. Ultimately, these studies enabled the development of an (SPhos)Pd-catalyzed decarbonylative difluoromethylation of aryl neopentylglycol boronate esters with difluoroacetyl fluoride.

Transmetalation

Reductive elimination

Oxidative addition

Catalytic cycle

Migratory insertion

Organometallic Chemistry

10.1021/jacs.1c08551

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Citations (41)

CCDC 1962368: Experimental Crystal Structure Determination

The Cambridge Structural Database (2020)

Christian A. Malapit Margarida Borrell Michael W. Milbauer Conor E. Brigham Melanie S. Sanford

10.5517/ccdc.csd.cc23w067

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