Photoredox cross-dehydrogenative C(sp2)-C(sp3) coupling of heteroarenes with secondary amines through 1,5-HAT

被引：1
|
作者：
Srinivasu, Vinjamuri [1 ]
Pattanaik, Swadhin [2 ]
Sureshkumar, Devarajulu [1 ]
机构：
[1] Indian Inst Sci Educ & Res Kolkata, Dept Chem Sci, Mohanpur 741246, West Bengal, India
[2] Indian Inst Sci Educ & Res, Dept Chem Sci, Berhampur 760010, Odisha, India
来源：
CHEMICAL COMMUNICATIONS | 2024年 / 60卷 / 72期
关键词：
METAL; TRANSITION; QUINOXALIN-2(1H)-ONES; DERIVATIVES; ALKYLATION;
D O I：
10.1039/d4cc02818j
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The functionalization of alpha-C(sp(3))-H bonds in amines has become a focal point of contemporary research. Here, we report a new approach utilizing photocatalysis alpha-C(sp(3))-H bond functionalization in alicyclic and aliphatic secondary amines facilitated by intramolecular 1,5-hydrogen atom transfer (HAT). This finding unlocks a sustainable method for rapidly constructing complex heterocyclics via cross-dehydrogenative C-C coupling of protected amines and nitrogen-containing heterocycles. This protocol boasts broad applicability to various substrates, exhibits tolerance to numerous functional groups, and supports the late-stage modification of drug molecules.
引用
收藏
页码：9757 / 9760
页数：4
相关论文
共 50 条
  • [41] Photoredox catalyzed C(sp3)-C(sp) coupling of dihydropyridines and alkynylbenziodoxolones
    Liang, Shengzong
    Angnes, Ricardo A.
    Potnis, Chinmay S.
    Hammond, Gerald B.
    TETRAHEDRON LETTERS, 2019, 60 (45)
  • [42] Pyridine-enabled copper-promoted cross dehydrogenative coupling of C(sp2)-H and unactivated C(sp3)-H bonds
    Wu, Xuesong
    Zhao, Yan
    Ge, Haibo
    CHEMICAL SCIENCE, 2015, 6 (10) : 5978 - 5983
  • [43] Cu-Catalyzed Cross-Dehydrogenative Coupling of Heteroaryl C(sp2)-H and Tertiary C(sp3)-H Bonds for the Construction of All-Carbon Triaryl Quaternary Centers
    Tang, Zhi
    Liu, Zhili
    Tong, Zhou
    Xu, Zhihui
    Au, Chak-Tong
    Qiu, Renhua
    Kambe, Nobuaki
    ORGANIC LETTERS, 2019, 21 (13) : 5152 - 5156
  • [44] Photoredox/Nickel Dual Catalysis for C(sp2)-C(sp3) Cross-Electrophile Coupling Reaction of Mesylates of Phenols and Primary Alcohols
    Jana, Sayan K.
    Bhattacharya, Rayan
    Dey, Purusattam
    Chakraborty, Sunit
    Maji, Biplab
    ACS CATALYSIS, 2024, 14 (18): : 14172 - 14182
  • [45] Cobalt-Catalyzed C(sp2)-C(sp3) Suzuki-Miyaura Cross Coupling
    Ludwig, Jacob R.
    Simmons, Eric M.
    Wisniewski, Steven R.
    Chirik, Paul J.
    ORGANIC LETTERS, 2021, 23 (03) : 625 - 630
  • [46] Enabling Deoxygenative C(sp2)-C(sp3) Cross-Coupling for Parallel Medicinal Chemistry
    Liu, Wei
    Mulhearn, James
    Hao, Bo
    Canellas, Santiago
    Last, Stefaan
    Gomez, Jose Enrique
    Jones, Alexander
    De Vera, Alexander
    Kumar, Kiran
    Rodriguez, Raquel
    Van Eynde, Lars
    Strambeanu, Iulia I.
    Wolkenberg, Scott E.
    ACS MEDICINAL CHEMISTRY LETTERS, 2023, 14 (06): : 853 - 859
  • [47] Nickel-Catalyzed Cross-Dehydrogenative Coupling of α-C(sp3)-H Bonds in N-Methylamides with C(sp3)-H Bonds in Cyclic Alkanes
    Li, Ze-Lin
    Sun, Kang-Kang
    Cai, Chun
    ORGANIC LETTERS, 2018, 20 (20) : 6420 - 6424
  • [48] CF3SO2Na-Mediated Visible-Light-Induced Cross-Dehydrogenative Coupling of Heteroarenes with Aliphatic C(sp3)-H Bonds
    Zeng, Cui-Lian
    Wang, Hao
    Gao, Di
    Zhang, Zhen
    Ji, Dong
    He, Wei
    Liu, Cheng-Kou
    Yang, Zhao
    Fang, Zheng
    Guo, Kai
    ORGANIC LETTERS, 2022, 24 (17) : 3244 - 3248
  • [49] Cobalt-NHC Catalyzed C(sp2)-C(sp3) and C(sp2)-C(sp2) Kumada Cross-Coupling of Aryl Tosylates with Alkyl and Aryl Grignard Reagents
    Piontek, Aleksandra
    Ochedzan-Siodlak, Wioletta
    Bisz, Elwira
    Szostak, Michal
    CHEMCATCHEM, 2021, 13 (01) : 202 - 206
  • [50] Palladium-Catalyzed Cross-Dehydrogenative Functionalization of C(sp2)-H Bonds
    Wu, Yinuo
    Wang, Jun
    Mao, Fei
    Kwong, Fuk Yee
    CHEMISTRY-AN ASIAN JOURNAL, 2014, 9 (01) : 26 - 47
12345