The dual alkylation of the C(sp3)-H bond of cyclic α-methyl-N-sulfonyl imines via the sequential condensation/hydride transfer/cyclization process

被引：21

作者：

Yuan, Kejin ^{[1
]}

Dong, Fengying ^{[1
]}

Yin, Xiangcong ^{[2
]}

Li, Shuai-Shuai ^{[1
,3
]}

Wang, Liang ^{[1
,3
]}

Xu, Lubin ^{[1
]}

机构：

[1] Qingdao Agr Univ, Coll Chem & Pharmaceut Sci, Qingdao 266109, Peoples R China

[2] Qingdao Univ, Affiliated Hosp, Hematol Diag Lab, Qingdao 266003, Shandong, Peoples R China

[3] Qingdao Univ Sci & Technol, Coll Chem & Mol Engn, Zhengzhou Rd 1153, Qingdao 266042, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2020年 / 7卷 / 23期

关键词：

ENANTIOSELECTIVE SYNTHESIS; DIASTEREOSELECTIVE SYNTHESIS; ARYLBORONIC ACIDS; 4+2 CYCLOADDITION; FUNCTIONALIZATION; KETIMINES; ALDEHYDES; CASCADE; CYCLOCONDENSATION; CONSTRUCTION;

D O I：

10.1039/d0qo00972e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The dual alkylation of the C(sp(3))-H bond of cyclic alpha-methyl-N-sulfonyl imines has been achieved through the piperidine-promoted cascade condensation/[1,5]-hydride transfer/cyclization sequence from cyclic alpha-methyl-N-sulfonyl imines and o-aminobenzaldehydes in trifluoroethanol, providing structurally diverse 3-cyclic N-sulfonyl imine substituted tetrahydroquinolines in good yields with excellent diastereoselectivities.

引用

页码：3868 / 3873

页数：6

共 50 条

[21] Sulfonyl Group-Induced Remote C(sp3)-N Bond Construction through Hydrogen Atom Transfer
Li, Haotian
Qiu, Xiancheng
Zhang, Xu
Wu, Xinxin
ORGANIC LETTERS, 2023, 25 (49) : 8814 - 8818
[22] C-H Bond Functionalization via Hydride Transfer: Lewis Acid Catalyzed Alkylation Reactions by Direct Intramolecular Coupling of sp3 C-H Bonds and Reactive Alkenyl Oxocarbenium Intermediates
McQuaid, Kevin M.
Sames, Dalibor
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (02) : 402 - +
[23] C-H bond functionalization via hydride transfer: Lewis acid catalyzed alkylation reactions by direct interamolecular coupling of sp3 C-H bonds and reactive alkenyl oxocarbenium intermediates
McQuaid, Kevin M.
Sames, Dalibor
Journal of the American Chemical Society, 2009, 131 (02): : 402 - 403
[24] Quinoline as an Intramolecular Hydride Shuttle in the Deoxygenative Coupling Reaction of Alcohol and the Inert Methyl C(sp3)-H Bond
Wang, Hui-Yun
Liu, Zhen-Yuan
Wang, Long-Xue
Shao, Da-Ying
Dong, Feng-Ying
Shen, Yao-Bin
Qiu, Bin
Xiao, Jian
An, Xiao-De
JOURNAL OF ORGANIC CHEMISTRY, 2024,
[25] C-H Bond Functionalization via Hydride Transfer: Direct Coupling of Unactivated Alkynes and sp3 C-H Bonds Catalyzed by Platinum Tetraiodide
Vadola, Paul A.
Sames, Dalibor
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (45) : 16525 - 16528
[26] Direct Access to 9/6-Fused Cycles via Sequential Hydride Shift Mediated Double C(sp3)-H Bond Functionalization
Nakamura, Issei
Anada, Masahiro
Sueki, Shunsuke
Makino, Kosho
Mori, Keiji
ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (04) : 502 - 507
[27] C-H bond functionalization via hydride transfer: Direct coupling of unactivated alkynes and sp3 C-H bonds catalyzed by Platinum tetraiodide
Vadola, Paul A.
Sames, Dalibor
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 239
[28] Rapid Access to 3-Aryltetralin Skeleton via C(sp3)-H Bond Functionalization: Investigation on the Substituent Effect of Aromatic Ring Adjacent to C-H Bond in Hydride Shift/Cyclization Sequence
Mori, Keiji
Sueoka, Shosaku
Akiyama, Takahiko
CHEMISTRY LETTERS, 2011, 40 (12) : 1386 - 1388
[29] Iron-Catalyzed Regioselective α-C-H Alkylation of N-Methylanilines: Cross-Dehydrogenative Coupling between Unactivated C(sp3)-H and C(sp3)-H Bonds via a Radical Process
Li, Ze-Lin
Sun, Kang-Kang
Wu, Peng-Yu
Cai, Chun
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (11): : 6830 - 6839
[30] From Isocyanides to Iminonitriles via Silver-mediated Sequential Insertion of C(sp3)-H Bond
Chi, Huiwen
Li, Hao
Liu, Bingxin
Ye, Rongxuan
Wang, Haoyang
Guo, Yin-Long
Tan, Qitao
Xu, Bin
ISCIENCE, 2019, 21 : 650 - +

← 1 2 3 4 5 →