Article
Chemistry, Applied
Paula Andrade-Sampedro, Jon M. Matxain, Arkaitz Correa
Summary: The development of catalytic tools for the late-stage modification of amino acids within a peptide framework is challenging but important. The researchers reported a Ru-catalyzed C(sp(2))-H hydroxylation method for di- and tripeptides containing tyrosine, using a carbamate as a removable directing group and PhI(OCOCF3)(2) (PIFA) as an oxidant. This method is reliable, scalable, and enables the synthesis of L-DOPA peptidomimetics without racemization. Density Functional Theory calculations support the proposed catalytic cycle involving Ru(II)/Ru(IV).
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Yulei Wang, Hendrik Simon, Xinran Chen, Zhipeng Lin, Shan Chen, Lutz Ackermann
Summary: While electrochemical ortho-selective C-H activations are well established, the development of distal C-H activations is still limited. In this study, we report the electrochemical meta-C-H functionalization, achieving remote C-H bromination in an undivided cell under ligand- and electrolyte-free conditions. Notably, pyrazolylarenes were selectively brominated at the benzenoid moiety rather than the electron-rich pyrazole ring for the first time. Mechanistic studies suggested the formation of a ruthenacycle followed by a ligand-to-ligand hydrogen transfer (LLHT) process.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Philip L. Hahn, Jared M. Lowe, Yubo Xu, Kevin L. Burns, Michael K. Hilinski
Summary: In this study, an organocatalytic approach using secondary amines as catalysts foroxaziridinium-mediated C-H hydroxylation is introduced. The operationally simple catalytic strategy demonstrated advantages in achieving high yielding and highly selective remote hydroxylation of compounds with oxidation-sensitive functional groups. Hexafluoroisopropanol was used as the solvent in the absence of water, leading to a proposed hydrogen-bonding effect that resulted in high chemoselectivity for remote aliphatic hydroxylation of 2 degrees alcohols.
Article
Chemistry, Multidisciplinary
Xue-Ya Gou, Yuke Li, Wei-Yu Shi, Yu-Yong Luan, Ya-Nan Ding, Yang An, Yan-Chong Huang, Bo-Sheng Zhang, Xue-Yuan Liu, Yong-Min Liang
Summary: This paper describes a new ruthenium-catalyzed method for the ortho- and meta-C-Ar-H glycosylation, resulting in the synthesis of various C-aryl pyranosides and furanosides. The method shows broad substrate scope and compatibility with different N-heterocyclic directing groups. Mechanistic studies suggest different pathways for ortho- and meta-C-Ar-H glycosylation, and density functional theory calculations provide an explanation for the high stereoselectivity observed in the meta-C-Ar-H glycosylation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Xue-Ya Gou, Yuke Li, Yu-Yong Luan, Wei-Yu Shi, Cui-Tian Wang, Yang An, Bo-Sheng Zhang, Yong-Min Liang
Summary: This study reports the combination of free radical cyclization and ruthenium-catalyzed meta-selective C-H functionalization for the synthesis of arylpyrrolidone derivatives, demonstrating high meta-site selectivity and wide applicability.
Article
Chemistry, Physical
Roman V. Ottenbacher, Denis G. Samsonenko, Anna A. Bryliakova, Andrey A. Nefedov, Konstantin P. Bryliakov
Summary: This study reports the selective oxidative functionalization of several steroids with a common gonane core by using chiral Mn complexes and H2O2 as the oxidant. Depending on the catalyst's steric demand and chirality, mono-hydroxylation at A, B, or C rings can be achieved with up to 58% yield. The use of hexafluoroisopropanol (HFIP) protects the C17-OH group in one of the steroids, allowing the synthesis of dihydroxy androstane derivatives without the need for protecting groups.
JOURNAL OF CATALYSIS
(2023)
Article
Chemistry, Physical
Manikantha Maraswami, Hajime Hirao, Teck-Peng Loh
Summary: This study achieved meta-arylation of phenols through copper catalysis with complete meta-selectivity and good tolerance towards various functional groups. Computational studies revealed that the reaction proceeded via a Heck-like pathway.
Article
Chemistry, Organic
Dmitry P. Lubov, Mikhail V. Shashkov, Andrey A. Nefedov, Konstantin P. Bryliakov
Summary: This study reports direct oxygenation of nonactivated aliphatic C-(sp(3))-H groups with peroxycarboxylic acids in the presence of palladium tris(pyridylmethyl)amine complex, resulting in hydroxylated derivatives with yields up to 94%. The oxidation of 3 degrees C-H groups shows stereospecificity and the catalyst system is highly sensitive to electronic effects. This suggests potential applications in the regioselective oxidative functionalization of complex molecules of natural origin.
Article
Chemistry, Multidisciplinary
Tian-Sheng Chen, Hao Long, Yuxing Gao, Hai-Chao Xu
Summary: The paper presents a practical and cost-efficient method using continuous flow reactors for the highly selective monooxygenation of benzylic C(sp(3))-H bonds. The method does not require catalysts or chemical oxidants, and the produced alcohols undergo facile hydrolysis. It exhibits a broad scope and exceptional site selectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Tian-Sheng Chen, Hao Long, Yuxing Gao, Hai-Chao Xu
Summary: This study presents a practical and cost-efficient electrochemical method for the highly selective monooxygenation of benzylic C(sp(3))-H bonds using continuous flow reactors. The method produces trifluoroacetate esters that are resistant to further oxidation but can be easily hydrolyzed to form benzylic alcohols during aqueous workup. It exhibits broad scope, exceptional site selectivity, and requires no catalysts or chemical oxidants.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Peng-Cheng Cui, Zheng-Chun Yin, Guan-Wu Wang
Summary: The visible-light-promoted C4-selective phosphorylation of unprefunctionalized pyridine and quinoline derivatives has been achieved. This Minisci-type protocol offers highly regioselective access to C4-phosphorylation products with good functional group tolerance and moderate to good yields via cross dehydrogenation coupling under mild conditions. Mechanistic studies demonstrate that the C4-phosphorylation products are obtained through a radical pathway.
Article
Chemistry, Multidisciplinary
Alexia Ville, Julien Annibaletto, Sebastien Coufourier, Christophe Hoarau, Rodolphe Tamion, Guillaume Journot, Cedric Schneider, Jean-Francois Briere
Summary: An efficient palladium-catalyzed C-H halogenation directed by primary amine has been reported for phenylalanine derivatives, with the extension to more challenging native phenylalanine demonstrated. Suitable conditions using trifluoroacetic acid as an additive were employed for this ortho-selective halogenation.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Editorial Material
Chemistry, Multidisciplinary
Alexia Ville, Julien Annibaletto, Sebastien Coufourier, Christophe Hoarau, Rodolphe Tamion, Guillaume Journot, Cedric Schneider, Jean-Francois Briere
Summary: An efficient palladium-catalyzed C-H halogenation of phenylalanine derivatives was achieved by employing primary-amine-directed strategy and suitable conditions with trifluoroacetic acid as additive, even extending to the more challenging native phenylalanine.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Physical
Xinyan Lv, Yaohang Cheng, Yingxiao Zong, Qingyun Wang, Guanghui An, Junke Wang, Guangming Li
Summary: In this study, a visible-light-mediated Ru-catalyzed para-alkylation of anilines was reported. The reaction showed high efficiency and mild conditions, with good functional group tolerance for late-stage functionalization of natural products and drugs.
Article
Chemistry, Multidisciplinary
Joe Higham, James A. Bull
Summary: Transient directing groups (TDGs) combined with copper have been used for efficient C-H functionalization without additional steps for directing group introduction and removal. This method demonstrates high regioselectivity in the beta-C(sp(2))-H sulfonylation and gamma-(peri)-sulfonylation reactions of benzaldehydes and achieves through the use of catalytic beta-alanine and sulfinate salts, with copper fluoride serving as both the copper source and oxidant.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Biochemistry & Molecular Biology
Samuel D. Banister, Mitchell Longworth, Richard Kevin, Shivani Sachdev, Marina Santiago, Jordyn Stuart, James B. C. Mack, Michelle Glass, Iain S. McGregor, Mark Connor, Michael Kassiou
ACS CHEMICAL NEUROSCIENCE
(2016)
Article
Toxicology
Mitchell Longworth, Samuel D. Banister, James B. C. Mack, Michelle Glass, Mark Connor, Michael Kassiou
FORENSIC TOXICOLOGY
(2016)
Article
Chemistry, Multidisciplinary
Adrian Varela-Alvarez, Tzuhsiung Yang, Heather Jennings, Katherine P. Kornecki, Samantha N. Macmillan, Kyle M. Lancaster, James B. C. Mack, J. Du Bois, John F. Berry, Djamaladdin G. Musaev
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2016)
Article
Chemistry, Medicinal
Kaitlin J. Basham, Vasudev R. Bhonde, Collin Kieffer, James B. C. Mack, Matthew Hess, Bryan E. Welm, Ryan E. Looper
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2014)
Article
Chemistry, Organic
Ryan E. Looper, Travis J. Haussener, James B. C. Mack
JOURNAL OF ORGANIC CHEMISTRY
(2011)
Article
Chemistry, Multidisciplinary
James B. C. Mack, T. Aaron Bedell, Ryan J. DeLuca, Graham A. B. Hone, Jennifer L. Roizen, Charles T. Cox, Erik J. Sorensen, J. Du Bois
JOURNAL OF CHEMICAL EDUCATION
(2018)
Article
Chemistry, Multidisciplinary
James B. C. Mack, Katherine L. Walker, Sophia G. Robinson, Richard N. Zare, Matthew S. Sigman, Robert M. Waymouth, J. Du Bois
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2019)
Article
Chemistry, Organic
Sophia G. Robinson, James B. C. Mack, Sara N. Alektiar, J. Du Bois, Matthew S. Sigman
Correction
Chemistry, Multidisciplinary
James B. C. Mack, John D. Gipson, J. Du Bois, Matthew S. Sigman
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Meeting Abstract
Chemistry, Multidisciplinary
Sophia Robinson, James Mack, Justin Du Bois, Matthew Sigman
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY
(2019)
Meeting Abstract
Chemistry, Multidisciplinary
Charles T. Cox, Justin DuBois, James Mack, Caitlin Ortega, Spencer Nam, Jenny Koenig
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY
(2014)
