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Allylic Functionalization

science.2024.385.issue-6713.largecover.jpg

Palladium-catalyzed cross-coupling of alcohols with olefins by positional tuning of a counteranion

Sven H. M. Kaster, Lei Zhu, William L. Lyon, Rulin Ma, Stephen E. Ammann, and M. Christina White

Supplementary Information
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Lei Zhu, Rulin Ma, 

Stephen Ammann 

(on wall)

Sven Kaster, Princeton, MacMillan Group

William Lyon,

Princeton, 

MacMillan Group

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Supplementary Information

Allylic C–H amination cross-coupling furnishes tertiary amines by electrophilic metal catalysis

S.Z. Ali, B.G. Budaitis, D.F. A. Fontaine, A.L. Pace, J.A. Garwin and M.C. White

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Brenna Budaitis

White Lab, UIUC

Siraj Ali

Radosevich Lab, MIT

Devon Fontaine

White Lab, UIUC

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Synthesis of anti-1,3 Amino Alcohol Motifs via Pd(II)/SOX Catalysis with the Capacity for Stereodivergence
Rulin Ma, Jonathon Young, Rossella Promontorio†, Friederike M. Dannheim, Christopher C. Pattillo and M. Christina White

Supplementary Information
Supplementary Information
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Rulia Ma

BMS,

Medicinal Chemitry

Rossella Promontorio

Pfizer Pharmaceuticals 

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Friederike Dannheim 

Cambridge University, Scientist at AstraZeneca

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Asymmetric Allylic C–H Alkylation via Palladium(II)/Chiral Sulfoxide-Oxazoline Catalysis

Wei Liu, Siraj Ali, Stephen Ammann, M. Christina White

Supplementary Information
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Siraj Ali

Radosevich Lab, MIT

Stephen Ammann

Research Scientist

Gilead

Wei Liu

Princeton, MacMillan Labs, Janssen Pharmaceuticals

Pd 2 Asymmetric allylic C-H alkylation via Pd 2018 (Pd 2).png
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C–H to C–N Cross-Coupling of Sulfonamides with Olefins

Rulin Ma and M. Christina White

Supplementary Information
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Rulia Ma

BMS,

Medicinal Chemistry

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Enantioselective Allylic C–H Oxidation of Terminal Olefins to Isochromans by Palladium(II)/Chiral Sulfoxide Catalysis

Stephen E. Ammann, Wei Liu, and M. Christina White

Supplementary Information
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Stephen Ammann

Research Scientist

Gilead

Wei Liu

Princeton, MacMillan Labs, Janssen Pharmaceuticals

Pd 4 Enantioselective Allylic C-H oxidation of terminal olefins to isochromans (Pd 4).png
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Aerobic Linear Allylic C–H Amination: Overcoming Benzoquinone Inhibition

Christopher C. Pattillo, Iulia I. Strambeanu, Pilar Calleja, Nicolaas A. Vermeulen, Tomokazu Mizuno, and M. Christina White

Supplementary Information
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Iulia Strambeanu

Discovery Chemistry, 

Janssen Pharmaceuticals

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Nicolaas Vermeulen

Corteva,

Agro Sciences

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N-Boc Amines to Oxazolidinones via Pd(II)/Bis-sulfoxide/Brønsted Acid Co-Catalyzed Allylic C–H Oxidation

Thomas J. Osberger and M. Christina White

Supplementary Information
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Thomas Osberger

Assistant Professor,

Cal Poly Pomona

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Terminal Olefins to Chromans, Isochromans, and Pyrans via Allylic C–H Oxidation

Stephen E. Ammann, Grant T. Rice, and M. Christina White

Supplementary Information
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Stephen Ammann

Gilead

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Grant Rice

Fish & Richardson,

Associate

Pd 7 Terminal Olefins to Chromans (Pd 7).png
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General Allylic C–H Alkylation with Tertiary Nucleophiles

Jennifer M. Howell, Wei Liu, Andrew J. Young, M. Christina White

Supplementary Information
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Jennifer Howell

Eli-Lilly,

Discovery Chemistry

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Andrew Young 

Dow Chemistry

Catalysis Discovery

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Wei Liu

Princeton, MacMillan Labs, Janssen Pharmaceuticals

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Catalyst-Controlled C−O versus C−N Allylic Functionalization of Terminal Olefins

Iulia I. Strambeanu and M. Christina White

Supplementary Information
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Iulia Strambeanu

Discovery Chemistry, 

Janssen Pharmaceuticals

Pd 9 C-O vs C-N Functionalization (Pd 9).png
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Terminal Olefins to Linear a,B-Unsaturated Ketones: Pd(II)/Hypervalent Iodine Co-catalyzed Wacker Oxidation-Dehydrogenation

M. A. Bigi and M. C. White

Supplementary Information
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Marinus Bigi

Catalysis Discovery,

Dow Chemical

Pd 10 Terminal Olefines to linear unsaturated ketones (Pd 10).png
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Sequential Allylic C-H Amination/Vinylic C-H Arylation: A Strategy for Unnatural Amino Acid Synthesis from a-Olefins

C. Jiang, D. J. Covell, A. F. Stepan, M S. Plummer, and M. C. White

Supplementary Information
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Dustin Covell

St. John's University, NYC

Assistant Professor

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Chao Jiang

Nanjing University Associate Professor

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Molecular Complexity via C-H Activation: A Dehydrogenative Diels-Alder Reaction

E. M. Stang and M. C. White

Supplementary Information
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Erik Stang

Oblon

 Patent Agent

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Synthetic Versatility in CH Oxidation A Rapid Approach to Differentiated Diols and Pyrans

Synthetic Versatility in C-H Oxidation: A Rapid Approach to Differentiated Diols and Pyrans from Simple Olefins

P. E. Gormisky and M. C. White

Supplementary Information
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Paul Gormisky

Bristol Myers Squibb

Senior Principal  Scientist

Pd 13 Diols and Pyrans from Olefins.png
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Allylic C-H Alkylation of Unactivated α-Olefins: Serial Ligand Catalysis Resumed

A. J. Young and M. C. White

Supplementary Information
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Andrew Young

Catalysis Discovery,

Dow Chemical

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Synthesis of Complex Allylic Esters via C-H Oxidation vs C-C Bond Formation

N.A. Vermeulen, J.H. Delcamp and M.C.White

Supplementary Information
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Nicolaas Vermeulen

Corteva,

Agro Sciences

Pd 15 C-H Allylic Esters via C-H oxidation .png
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Diversification of a β-lactam pharmacophore via allylic C-H amination: accelerating effect of Lewis acid co-catalyst

X. Qi, G. T. Rice, M. S. Lall, M. S. Plummer, M. C. White

Supplementary Information
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Grant Rice

Fish & Richardson,

Associate

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Allylic C-H Amination for Preparation of syn-1,3-Amino Alcohol Motifs

G.T. Rice and M.C. White

Supplementary Information
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Grant Rice

Fish & Richardson,

Associate

Pd 17 Prep of 1,3 amino alcohols (syn).png
Pub 15.png
Supplementary Information
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Sean Reed

Wilson Sonsini Goodrich & Rosati

Patent Agent

Anthony Mazzotti

PTC Therapeutics

Pd 18  Intermolecular amination w_ bronstead base.png
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Catalytic Intermolecular Allylic C-H Alkylation

A.J. Young and M.C. White

Supplementary Information
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Andrew Young 

Dow Chemistry

Catalysis Discovery

Pd 19 Catalytic intermolecular allylic alkylation.png
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A Chiral Lewis Acid Strategy for Enantioselective Allylic C-H Oxidation

D.J. Covell and M.C. White

Supplementary Information
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Dustin Covell

St. John's University, NYC

Assistant Professor

Pd 20 Chiral LA C-H oxidation.png
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Catalytic Intermolecular Linear Allylic C-H Amination via Heterobimetallic Catalysis

S.A. Reed and M.C. White

Supplementary Information
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Sean Reed

Wilson Sonsini Goodrich & Rosati

Patent Agent

Pd 21 Intermolecular C-H amination via heterobimetallic catalysis.png
A General and Highly Selective Chelate-Controlled Intermolecular Oxidative Heck Reaction c

syn-1,2-Amino Alcohols via Diastereoselective Allylic C-H Amination

K.J. Fraunhoffer and M.C. White.

Supplementary Information
pub7.jpg

Ken Fraunhoffer
Bristol-Myers Squibb, NJ

Process Investigator III

Pd 22 1,2-amino alcohols (syn).png
A General and Highly Selective Chelate-Controlled Intermolecular Oxidative Heck Reaction c

Serial Ligand Catalysis: A Highly Selective Allylic C-H Oxidation

M.S. Chen; N. Prabagaran; N.A. Labenz; and M.C. White

Supplementary Information
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Mark Chen

Lehigh University

Assistant Professor

Prabagaran Narayanasamy

Pvitalz

President and CEO

Nathan Labenz

Waymark

AI R&D, CEO

Pd 23 Serial ligand catalysis.png
A General and Highly Selective Chelate-Controlled Intermolecular Oxidative Heck Reaction c

A Sulfoxide-Promoted, Catalytic Method for the Regioselective Synthesis of Allylic Acetates from Monosubstituted Olefins via C-H Oxidation

M.S. Chen; M.C. White

Supplementary Information
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Mark Chen

Lehigh University

Assistant Professor

Pd 24 Sulfoxide promoted synthesis of allylic acetates (1).png

Oxidative Heck

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Oxidative Heck Vinylation for the Synthesis of Complex Dienes and Polyenes

J. H. Delcamp, P. E. Gormisky, and M. C. White

Supplementary Information
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Jared Delcamp

University of Mississippi

Associate Professor

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Paul Gormisky

Bristol Myers Squibb

Senior Principal Scientist

OH1vinylation for the synthesis of complex dienes and polyenes.png
A General and Highly Selective Chelate-Controlled Intermolecular Oxidative Heck Reaction c

A General and Highly Selective Chelate-Controlled Intermolecular Oxidative Heck Reaction

J.H. Delcamp; A.P. Brucks; and M.C. White

Supplementary Information
Jared & Alex Publication.png

Jared Delcamp

University of Mississippi

Associate Professor

Alex Brucks

Pfizer

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Sequential Hydrocarbon Functionalization Allylic CH OxidationVinylic CH Arylation cover.jp

Sequential Hydrocarbon Functionalization: Allylic C−H Oxidation/Vinylic C−H Arylation

J.H. Delcamp and M.C. White

Supplementary Information
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Jared Delcamp

University of Mississippi

Associate Professor

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