Allylic Functionalization

Science, 2024, Volume 385 Issue 6713

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

Lei Zhu, Rulin Ma,

Stephen Ammann

(on wall)

Sven Kaster, Princeton, MacMillan Group

William Lyon,

Princeton,

MacMillan Group

Science, 2022, 376(6590), 276–283.

Science, 2022, 376(6590), 276–283. https://doi.org/10.1126/science.abn8382

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

Brenna Budaitis

White Lab, UIUC

Siraj Ali

Radosevich Lab, MIT

Devon Fontaine

White Lab, UIUC

J. Am. Chem. Soc., 2019, 141 (24), 9468-9473

J. Am. Chem. Soc., 2019, 141 (24), 9468-9473, DOI: 10.1021/jacs.9b02690

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

Rulia Ma

BMS,

Medicinal Chemitry

Rossella Promontorio

Pfizer Pharmaceuticals

Friederike Dannheim

Cambridge University, Scientist at AstraZeneca

Pd 1 Pd 1 anti 1,3- Amino alcohols 2019 (Pd 1) .png

J. Am. Chem. Soc., 2018, 140, 10658

J. Am. Chem. Soc., 2018, 140, 10658, DOI: 10.1021/jacs.8b05668

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

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

Supplementary Information

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

J. Am. Chem. Soc., 2018, 140, 3202

J. Am. Chem. Soc., 2018, 140, 3202, DOI: 10.1021/jacs.7b13492

C–H to C–N Cross-Coupling of Sulfonamides with Olefins

Rulin Ma and M. Christina White

Supplementary Information

Rulia Ma

BMS,

Medicinal Chemistry

Pd 3 C-H to C-N Cross Couplings (Pd 3).png

Angew. Chem. Int. Ed., 2016, 55, 9571,

Angew. Chem. Int. Ed., 2016, 55, 9571, DOI: 10.1002/anie.201603576

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

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

J. Am. Chem. Soc., 2016, 138, 1265

J. Am. Chem. Soc., 2016, 138, 1265, DOI: 10.1021/jacs.5b11294

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

Iulia Strambeanu

Discovery Chemistry,

Janssen Pharmaceuticals

Nicolaas Vermeulen

Corteva,

Agro Sciences

Pd 5 Aerobic Linear Allylic Amination (Pd 5).png

J. Am. Chem. Soc., 2014, 136, 11176

J. Am. Chem. Soc., 2014, 136, 11176, DOI: 10.1021/ja506036q

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

Thomas Osberger

Assistant Professor,

Cal Poly Pomona

Pd 6 N Boc amines to oxazolidinones (Pd 6).png

J. Am. Chem. Soc., 2014, 136, 10834

J. Am. Chem. Soc., 2014, 136, 10834, DOI: 10.1021/ja503322e

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

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

Supplementary Information

Stephen Ammann

Gilead

Grant Rice

Fish & Richardson,

Associate

Pd 7 Terminal Olefins to Chromans (Pd 7).png

J. Am. Chem. Soc., 2014, 136, 5750

J. Am. Chem. Soc., 2014, 136, 5750, DOI: 10.1021/ja500726e

General Allylic C–H Alkylation with Tertiary Nucleophiles

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

Supplementary Information

Jennifer Howell

Eli-Lilly,

Discovery Chemistry

Andrew Young

Dow Chemistry

Catalysis Discovery

Wei Liu

Princeton, MacMillan Labs, Janssen Pharmaceuticals

Pd 8General Allylic Alkylation (Pd 8).png

J. Am. Chem. Soc., 2013, 135, 12032

J. Am. Chem. Soc., 2013, 135, 12032, DOI: 10.1021/ja405394v

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

Iulia I. Strambeanu and M. Christina White

Supplementary Information

Iulia Strambeanu

Discovery Chemistry,

Janssen Pharmaceuticals

Pd 9 C-O vs C-N Functionalization (Pd 9).png

J. Am. Chem. Soc., 2013, 135, 7831

J. Am. Chem. Soc., 2013, 135, 7831, DOI: 10.1021/ja402651q

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

Marinus Bigi

Catalysis Discovery,

Dow Chemical

Pd 10 Terminal Olefines to linear unsaturated ketones (Pd 10).png

Organic Letters, 2012, 14, 1386

Organic Letters, 2012, 14, 1386, DOI: 10.1021/ol300063t

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

Dustin Covell

St. John's University, NYC

Assistant Professor

Chao Jiang

Nanjing University Associate Professor

Pd 11 Strategy for Unnatural Amino Acids.png

J. Am. Chem. Soc., 2011, 133, 14892

J. Am. Chem. Soc., 2011, 133, 14892 DOI: 10.1021/ja2059704

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

E. M. Stang and M. C. White

Supplementary Information

Erik Stang

Oblon

Patent Agent

J. Am. Chem. Soc., 2011, 133, 12584

J. Am. Chem. Soc., 2011, 133, 12584 DOI: 10.1021/ja206013j

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

Paul Gormisky

Bristol Myers Squibb

Senior Principal Scientist

Angew. Chem. Int. Ed., 2011, 50, 6824

Angew. Chem. Int. Ed., 2011, 50, 6824 DOI: 10.1002/anie.201101654

Allylic C-H Alkylation of Unactivated α-Olefins: Serial Ligand Catalysis Resumed

A. J. Young and M. C. White

Supplementary Information

Andrew Young

Catalysis Discovery,

Dow Chemical

Pd 14 C-H alkylation of unactivated olefins.png

JACS, 2010, 132, 11323

JACS, 2010, 132, 11323 DOI: 10.1021/ja104826g

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

Nicolaas Vermeulen

Corteva,

Agro Sciences

Pd 15 C-H Allylic Esters via C-H oxidation .png

Tetrahedron, 2010, 66, 4816

Tetrahedron, 2010, 66, 4816 DOI: 10.1016/j.tet.2010.04.064

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

Grant Rice

Fish & Richardson,

Associate

J. Am. Chem. Soc., 2009, 131, 33, 11707–11711

J. Am. Chem. Soc., 2009, 131, 33, 11707–11711 DOI: 10.1021/ja9054959

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

G.T. Rice and M.C. White

Supplementary Information

Grant Rice

Fish & Richardson,

Associate

Pd 17 Prep of 1,3 amino alcohols (syn).png

J. Am. Chem. Soc., 2009, 131, 33, 11701–11706

J. Am. Chem. Soc., 2009, 131, 33, 11701–11706 DOI: 10.1021/ja903939k

A Catalytic, Bronsted Base Strategy for Intermolecular Allylic C-H Amination

S.A. Reed; A.R. Mazzotti; and M.C. White

Supplementary Information

Sean Reed

Wilson Sonsini Goodrich & Rosati

Patent Agent

Anthony Mazzotti

PTC Therapeutics

Pd 18 Intermolecular amination w_ bronstead base.png

J. Am. Chem. Soc., 2008, 130, 43, 14090–14091

J. Am. Chem. Soc., 2008, 130, 43, 14090–14091 DOI: 10.1021/ja806867p

Catalytic Intermolecular Allylic C-H Alkylation

A.J. Young and M.C. White

Supplementary Information

Andrew Young

Dow Chemistry

Catalysis Discovery

Pd 19 Catalytic intermolecular allylic alkylation.png

ACIEE, 2008, 47(34), 6448–6451

ACIEE, 2008, 47(34), 6448–6451 DOI: 10.1002/anie.200802106

A Chiral Lewis Acid Strategy for Enantioselective Allylic C-H Oxidation

D.J. Covell and M.C. White

Supplementary Information

Dustin Covell

St. John's University, NYC

Assistant Professor

J. Am. Chem. Soc., 2008, 130, 3316

J. Am. Chem. Soc., 2008, 130, 3316 DOI: 10.1021/ja710206u

Catalytic Intermolecular Linear Allylic C-H Amination via Heterobimetallic Catalysis

S.A. Reed and M.C. White

Supplementary Information

Sean Reed

Wilson Sonsini Goodrich & Rosati

Patent Agent

Pd 21 Intermolecular C-H amination via heterobimetallic catalysis.png

J. Am. Chem. Soc., 2007, 129, 7274-7276

J. Am. Chem. Soc., 2007, 129, 7274-7276 DOI: 10.1021/ja071905g

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

Ken Fraunhoffer
Bristol-Myers Squibb, NJ

Process Investigator III

J. Am. Chem. Soc., 2006, 128, 8989-9258 DOI: 10.1021/ja063096

Macrolactonization via Hydrocarbon Oxidation

Kenneth J. Fraunhoffer, Prabagaran Narayanasamy, Lauren E. Sirois,† and M. Christina White

Supplementary Information

Ken Fraunhoffer
Bristol-Myers Squibb, NJ

Process Investigator III

J. Am. Chem. Soc., 2005, 127, 6970-6971

J. Am. Chem. Soc., 2005, 127, 6970-6971 DOI: 10.1021/ja0500198

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

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

Supplementary Information

Mark Chen

Lehigh University

Assistant Professor

Prabagaran Narayanasamy

Pvitalz

President and CEO

Nathan Labenz

Waymark

AI R&D, CEO

J. Am. Chem. Soc. 2004, 126, 1346-1347

J. Am. Chem. Soc. 2004, 126, 1346-1347 DOI: 10.1021/ja039107n

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

Mark Chen

Lehigh University

Assistant Professor

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

Oxidative Heck

J. Am. Chem. Soc., 2013, 135, 8460

J. Am. Chem. Soc., 2013, 135, 8460, DOI: 10.1021/ja402891m

Oxidative Heck Vinylation for the Synthesis of Complex Dienes and Polyenes

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

Supplementary Information

Jared Delcamp

University of Mississippi

Associate Professor

Paul Gormisky

Bristol Myers Squibb

Senior Principal Scientist

OH1vinylation for the synthesis of complex dienes and polyenes.png

J. Am. Chem. Soc., 2008, 130, 34, 11270–11271 DOI: 10.1021/ja804120r

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

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

Supplementary Information

Jared Delcamp

University of Mississippi

Associate Professor

Alex Brucks

Pfizer

J. Am. Chem. Soc., 2006, 128, 15076-15077

J. Am. Chem. Soc., 2006, 128, 15076-15077 DOI: 10.1021/ja066563d

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

J.H. Delcamp and M.C. White

Supplementary Information

Jared Delcamp

University of Mississippi

Associate Professor