Photoredox catalysis enabled selective C-N bond cleavage in ring-strained tertiary amines

被引：0
作者：
Zhou, Yu [1 ,2 ]
Wang, Pu-Sheng [1 ,2 ]
机构：
[1] Univ Sci & Technol China, Hefei Natl Res Ctr Phys Sci Microscale, Hefei 230026, Peoples R China
[2] Univ Sci & Technol China, Dept Chem, Hefei 230026, Peoples R China
来源：
TETRAHEDRON LETTERS | 2025年 / 167卷
关键词：
Photoredox catalysis; C-N bond cleavage; Ring-strained tertiary amines; SOLID-PHASE SYNTHESIS; HYDROGEN-PEROXIDE; OXIDATIVE GENERATION; DEMETHYLATION; DEALKYLATION; MORPHINE; DEBENZYLATION; DERIVATIVES; CONVENIENT; MILD;
D O I：
10.1016/j.tetlet.2025.155666
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The selective cleavage of C-N bonds in tertiary amines to form secondary amines is a promising strategy for constructing diverse nitrogen-containing compounds. Herein, we introduce a simple method for the selective Ndealkylation of ring-strained tertiary amines under blue LED light irradiation using 4CzIPN as photocatalyst and CCl4 as oxidant with up to 99% yield.
引用
收藏
页数：5
相关论文
共 55 条
[1]   N-DEMETHYLATION OF MORPHINE AND STRUCTURALLY RELATED COMPOUNDS WITH CHLOROFORMATE ESTERS [J].
ABDELMONEM, MM ;
PORTOGHESE, PS .
JOURNAL OF MEDICINAL CHEMISTRY, 1972, 15 (02) :208-+
[2]   Reductive Amination in the Synthesis of Pharmaceuticals [J].
Afanasyev, Oleg, I ;
Kuchuk, Ekaterina ;
Usanov, Dmitry L. ;
Chusov, Denis .
CHEMICAL REVIEWS, 2019, 119 (23) :11857-11911
[3]   A mild and selective method for N-dealkylation of tertiary amines [J].
Bhat, RG ;
Ghosh, Y ;
Chandrasekaran, S .
TETRAHEDRON LETTERS, 2004, 45 (43) :7983-7985
[4]   PREPARATION AND SYNTHETIC UTILITY OF O-SUBSTITUTED NORMETHYLMORPHINES [J].
BOROWITZ, IJ ;
DIAKIW, V .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1975, 12 (06) :1123-1126
[5]   Oxidative Polymer Degradation via Cope Elimination [J].
Bowman, Jared I. ;
Young, James B. ;
Thompson, Victoria L. ;
Stewart, Kevin A. ;
Diodati, Lily E. ;
Stevens, Kaden C. ;
Eades, Cabell B. ;
Sumerlin, Brent S. .
MACROMOLECULES, 2024, 57 (15) :7547-7555
[6]  
Braun J.V., 1909, BER DTSCH CHEM GES, V42, P2035, DOI [10.1002/cber.19090420286, DOI 10.1002/CBER.19090420286]
[7]  
Braun J.V., 1900, BER DTSCH CHEM GES, V33, P1438
[8]   N-DEMETHYLATION OF MORPHINE AND CODEINE USING METHYL CHLOROFORMATE [J].
BRINE, GA ;
BOLDT, KG ;
HART, CK ;
CARROLL, FI .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1976, 8 (03) :103-106
[9]   Palladium-Catalyzed N-Demethylation/N-Acylation of Some Morphine and Tropane Alkaloids [J].
Carroll, Robert J. ;
Leisch, Hannes ;
Scocchera, Eric ;
Hudlicky, Tomas ;
Cox, D. Phillip .
ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (18) :2984-2992
[10]   Organophotocatalytic N-Demethylation of Oxycodone Using Molecular Oxygen [J].
Chen, Yuesu ;
Glotz, Gabriel ;
Cantillo, David ;
Kappe, C. Oliver .
CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (13) :2973-2979
123456