Co/NHPI-mediated aerobic oxygenation of benzylic C–H bonds in pharmaceutically relevant molecules

Hruszkewycz, Damian P.; Miles, Kelsey C.; Thiel, Oliver R.; Stahl, Shannon S.

doi:10.1039/c6sc03831j

Co/NHPI-mediated aerobic oxygenation of benzylic C–H bonds in pharmaceutically relevant molecules

Journal Article · Fri Oct 07 00:00:00 EDT 2016 · Chemical Science

DOI:https://doi.org/10.1039/c6sc03831j· OSTI ID:1429913

Hruszkewycz, Damian P. ^[1]; Miles, Kelsey C. ^[2]; Thiel, Oliver R. ^[3]; Stahl, Shannon S. ^[2]

Univ. of Wisconsin, Madison, WI (United States). Department of Chemistry; University of Wisconsin
Univ. of Wisconsin, Madison, WI (United States). Department of Chemistry
Process Development, Drug Substance Technologies, Amgen Inc., Thousand Oaks, CA (United States)

A simple cobalt(II)/N-hydroxyphthalimide catalyst system has been identified for selective conversion of benzylic methylene groups in pharmaceutically relevant (hetero)arenes to the corresponding (hetero)aryl ketones. The radical reaction pathway tolerates electronically diverse benzylic C–H bonds, contrasting recent oxygenation reactions that are initiated by deprotonation of a benzylic C–H bond. The reactions proceed under practical reaction conditions (1 M substrate in BuOAc or EtOAc solvent, 12 h, 90–100 °C), and they tolerate common heterocycles, such as pyridines and imidazoles. A cobalt-free, electrochemical, NHPI-catalyzed oxygenation method overcomes challenges encountered with chelating substrates that inhibit the chemical reaction. The utility of the aerobic oxidation method is showcased in the multigram synthesis of a key intermediate towards a drug candidate (AMG 579) under process-relevant reaction conditions.

View Accepted Manuscript (DOE)

Research Organization:: Univ. of Wisconsin, Madison, WI (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)

Grant/Contract Number:: FG02-05ER15690

OSTI ID:: 1429913

Journal Information:: Chemical Science, Journal Name: Chemical Science Journal Issue: 2 Vol. 8; ISSN 2041-6520; ISSN CSHCBM

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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Carbene-catalyzed enantioselective oxidative coupling of enals and di(hetero)arylmethanes Chen, Qiao; Zhu, Tingshun; Majhi, Pankaj Kumar Chemical Science, Vol. 9, Issue 46 https://doi.org/10.1039/c8sc03480j	journal	January 2018
Organic chemistry at anodes and photoanodes Reid, Lacey M.; Li, Tengfei; Cao, Yang Sustainable Energy & Fuels, Vol. 2, Issue 9 https://doi.org/10.1039/c8se00175h	journal	January 2018
Iron-catalyzed oxidative functionalization of C(sp ³ )–H bonds under bromide-synergized mild conditions Yu, Han; Zhao, Qixin; Wei, Zheyu Chemical Communications, Vol. 55, Issue 54 https://doi.org/10.1039/c9cc03939b	journal	January 2019
The Mn-catalyzed paired electrochemical facile oxychlorination of styrenes via the oxygen reduction reaction Tian, Siyu; Jia, Xiaofei; Wang, Ling Chemical Communications, Vol. 55, Issue 80 https://doi.org/10.1039/c9cc06746a	journal	January 2019
Cercosporin-bioinspired selective photooxidation reactions under mild conditions Li, Jia; Bao, Wenhao; Tang, Zhaocheng Green Chemistry, Vol. 21, Issue 22 https://doi.org/10.1039/c9gc02270h	journal	January 2019
Iodine-promoted one-pot synthesis of 1,3,4-oxadiazole scaffolds via sp ³ C–H functionalization of azaarenes Mani, Geeta Sai; Donthiboina, Kavitha; Shankaraiah, Nagula New Journal of Chemistry, Vol. 43, Issue 40 https://doi.org/10.1039/c9nj03573g	journal	January 2019
Oxidative C(sp ³ )–H functionalization of methyl-azaheteroarenes: a facile route to 1,2,4-triazolo[4,3- a ]pyridines Weng, Wei-Zhao; Gao, Yin-He; Zhang, Xue Organic & Biomolecular Chemistry, Vol. 17, Issue 8 https://doi.org/10.1039/c9ob00033j	journal	January 2019
Selective synthesis of (1 H -benzo[ d ]imidazol-2-yl)(phenyl)methanone and quinoxaline from aromatic aldehyde and o -phenylenediamine Zhan, Zhenzhen; Ma, Haojie; Cui, Xinfeng Organic & Biomolecular Chemistry, Vol. 17, Issue 20 https://doi.org/10.1039/c9ob00531e	journal	January 2019
Recent trends in catalytic sp ³ C–H functionalization of heterocycles Kaur, Milanpreet; Van Humbeck, Jeffrey F. Organic & Biomolecular Chemistry, Vol. 18, Issue 4 https://doi.org/10.1039/c9ob01559k	journal	January 2020
Aerobic conversion of benzylic sp ³ C–H in diphenylmethanes and benzyl ethers to CO bonds under catalyst-, additive- and light-free conditions Tian, Xinzhe; Cheng, Xinqiang; Yang, Xinzheng Organic Chemistry Frontiers, Vol. 6, Issue 7 https://doi.org/10.1039/c9qo00004f	journal	January 2019
Cobalt( ii )-catalyzed benzylic oxidations with potassium persulfate in TFA/TFAA Li, Tianlei; Li, Jishun; Zhu, Zihao RSC Advances, Vol. 9, Issue 36 https://doi.org/10.1039/c9ra03346g	journal	January 2019
Electrochemical C–H oxygenation and alcohol dehydrogenation involving Fe-oxo species using water as the oxygen source Das, Amit; Nutting, Jordan E.; Stahl, Shannon S. Chemical Science, Vol. 10, Issue 32 https://doi.org/10.1039/c9sc02609f	journal	January 2019
A series of highly stable porphyrinic metal–organic frameworks based on iron–oxo chain clusters: design, synthesis and biomimetic catalysis Liu, Gang; Cui, Hao; Wang, Sujuan Journal of Materials Chemistry A, Vol. 8, Issue 17 https://doi.org/10.1039/d0ta02033h	journal	January 2020
Oxidation of alkylarenes by modified graphite Behrouzi, Leila; Bagheri, Robabeh; Song, Zhenlun Materials Research Express, Vol. 6, Issue 12 https://doi.org/10.1088/2053-1591/ab54db	journal	November 2019

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