CeCl3-Catalyzed C-H Alkylation of N-Sulfonyl Ketimines with Alkanes and Ether via Photoinduced Ligand-to-Metal Charge Transfer

被引：0

作者：

Zhou, Bin ^{[1
]}

Dong, Min ^{[4
]}

Wang, Wei ^{[4
]}

Yu, Sha ^{[4
]}

Yue, Huilan ^{[2
,3
]}

Wei, Wei ^{[2
,3
]}

Yi, Dong ^{[4
]}

机构：

[1] Shaoyang Univ, Coll Pharm, Shaoyang 422099, Peoples R China

[2] Northwest Inst Plateau Biol, Qinghai Prov Key Lab Tibetan Med Res, Xining 810008, Qinghai, Peoples R China

[3] Northwest Inst Plateau Biol, CAS Key Lab Tibetan Med Res, Xining 810008, Qinghai, Peoples R China

[4] Southwest Med Univ, Sch Pharm, Green Pharmaceut Technol Key Lab Luzhou City, Luzhou 646000, Sichuan, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 24期

基金：

中国国家自然科学基金;

关键词：

CYCLIC ALDIMINES; FUNCTIONALIZATION; ALKENES;

D O I：

10.1021/acs.joc.4c02205

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A cerium-catalyzed C-H alkylation of N-sulfonyl ketimines with low-cost and readily available alkanes as alkyl sources was developed. This transformation proceeded through the synergy of photoinitiated ligand-to-metal charge transfer (LMCT) using a chlorine radical as an HAT reagent and air as a green oxidant. A series of alkylated N-sulfonyl ketimines were synthesized with moderate to good yields in a highly atom-economic manner under chemical oxidant-free conditions.

引用

页码：18337 / 18343

页数：7

共 50 条

[31] Palladium-Catalyzed Benzylic Addition of 2-Methyl Azaarenes to N-Sulfonyl Aldimines via C-H Bond Activation
Qian, Bo
Guo, Shengmei
Shao, Jianping
Zhu, Qiming
Yang, Lei
Xia, Chungu
Huang, Hanmin
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (11) : 3650 - +
[32] Ligand-to-Metal Charge Transfer (LMCT) Catalysis: Harnessing Simple Cerium Catalysts for Selective Functionalization of Inert C-H and C-C Bonds
An, Qing
Chang, Liang
Pan, Hui
Zuo, Zhiwei
ACCOUNTS OF CHEMICAL RESEARCH, 2024, 57 (19) : 2915 - 2927
[33] Organocatalyzed Double C(sp3)-H Alkylation of Cyclic N-Sulfonyl Ketimines with 3-Chloropropiophenones: Selective Access to 2,3,6-Trisubstituted Pyridines
Patel, Ashvani Kumar
Samanta, Sampak
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (33)
[34] Palladium-Catalyzed Tandem Dehydrogenative [4+2] Annulation of Terminal Olefins with N-Sulfonyl Amides via C-H Activations
Sun, Manman
Chen, Weida
Xia, Xiangyu
Shen, Guodong
Ma, Yongmin
Yang, Jianguo
Ding, Hanfeng
Wang, Zhiming
ORGANIC LETTERS, 2020, 22 (08) : 3229 - 3233
[35] Synthesis and anti-inflammatory evaluation of N-sulfonyl anthranilic acids via Ir(III)-catalyzed C-H amidation of benzoic acids
Han, Sang Hoon
Suh, Hyo Sun
Jo, Hyeim
Oh, Yongguk
Mishra, Neeraj Kumar
Han, Sangil
Kim, Hyung Sik
Jung, Young Hoon
Lee, Byung Mu
Kim, In Su
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2017, 27 (10) : 2129 - 2134
[36] Lewis Acidic Ionic-Liquid-Catalyzed Radical-Cascade Alkylation/Cyclization of N-Alkyl-N-methacryloyl Benzamides with Alkanes via Visible-Light-Induced Ligand-to-Metal Charge Transfer: Access to Alkylated Isoquinoline-1,3(2H,4H)-diones
Zhang, Tao
Ren, Xinxin
Li, Jingkun
Wang, Yanhong
Wang, Bin
Chen, Ziren
Xia, Yu
Wu, Shaofeng
Liu, Chenjiang
Zhang, Yonghong
ORGANIC LETTERS, 2024, 26 (48) : 10259 - 10266
[37] A new Ni-diaminoglyoxime-g-C3N4complex towards efficient photocatalytic ethanol splitting via a ligand-to-metal charge transfer (LMCT) mechanism
Xu, Yanqi
Du, Cui
Zhou, Chen
Yang, Shengyang
CHEMICAL COMMUNICATIONS, 2020, 56 (52) : 7171 - 7174
[38] Photoreactivity of (HBpyrazolyl3) TiCl3 and (C5H5)TiCl3 initiated by ligand-to-metal charge transfer excitation
Kunkely, H
Vogler, A
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 1998, 119 (03) : 187 - 190
[39] Iron-catalyzed N-alkylation of azoles via cleavage of an sp3 C-H bond adjacent to a nitrogen atom
Xia, Qinqin
Chen, Wanzhi
Journal of Organic Chemistry, 2012, 77 (20): : 9366 - 9373
[40] Iron-Catalyzed N-Alkylation of Azoles via Cleavage of an sp3 C-H Bond Adjacent to a Nitrogen Atom
Xia, Qinqin
Chen, Wanzhi
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (20): : 9366 - 9373

← 1 2 3 4 5 →