Rhodium-catalyzed addition reactions of benzylic C–H bonds to cyclic N-sulfonyl ketimines via π-coordination

被引:0
|
作者
Yuntong Li [1 ,2 ]
Hang Shi [2 ,3 ]
机构
[1] Department of Chemistry, Zhejiang University
[2] Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, Department of Chemistry, School of Science and Research Center for Industries of the Future, Westlake University
[3] Institute of Natural Sciences, Westlake Institute for Advanced Study
基金
中国国家自然科学基金;
关键词
D O I
暂无
中图分类号
O621.251 [];
学科分类号
070303 ; 081704 ;
摘要
Mannich-type reactions are a widely used method for the synthesis of amines due to the readily availability of nucleophiles and electrophiles. However, the inclusion of alkylarenes instead of active carbon pronucleophiles such as aldehydes and ketones in these addition reactions has been a challenge due to the inherent difficulty of benzylic deprotonation. In this study, we present a novel approach for the construction of N-sulfonyl amines via rhodium-catalyzed addition of unbiased benzylic C–H bonds to cyclic N-sulfonyl ketamines through π-coordination. This strategy enables the synthesis of a diverse range of N-sulfonyl amines, and subsequent diversification of the addition products showcases the synthetic potential of this protocol.
引用
收藏
页码:316 / 320
页数:5
相关论文
共 50 条
  • [21] Iridium-catalyzed direct C-H arylation of cyclic N-sulfonyl ketimines with arylsiloxanes at ambient temperature
    Sarkar, Writhabrata
    Bhowmik, Arup
    Das, Sumit
    Sulekha, Aiswarya Balaram
    Mishra, Aniket
    Deb, Indubhusan
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (36) : 7074 - 7078
  • [22] Iridium(III)-Catalyzed Selective and Mild C-H Amidation of Cyclic N-Sulfonyl Ketimines with Organic Azides
    Maraswami, Manikantha
    Chen, Gang
    Loh, Teck-Peng
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (03) : 416 - 421
  • [23] Rhodium-Catalyzed Cyclocarbonylation of Ketimines via C-H Bond Activation
    Gao, Bao
    Liu, Song
    Lan, Yu
    Huang, Hanmin
    ORGANOMETALLICS, 2016, 35 (10) : 1480 - 1487
  • [24] Rhodium-Catalyzed N-Arylation Addition of Arylboronic Acids to Ketimines
    Qian, Xue-Wei
    Sun, Xing-Wen
    CHINESE JOURNAL OF CHEMISTRY, 2024, 42 (18) : 2243 - 2248
  • [25] Rhodium-catalysed direct C-H allylation of N-sulfonyl ketimines with allyl carbonates
    Mei, Shu-Tao
    Wang, Nan-Jin
    Qin Ouyang
    Wei, Ye
    CHEMICAL COMMUNICATIONS, 2015, 51 (14) : 2980 - 2983
  • [26] 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 - +
  • [27] PdII-Catalyzed Spiroannulation of Cyclic N-Sulfonyl Ketimines with Aryl Iodides through C-H Bond Activation
    Reddy, K. Nagarjuna
    Rao, M. V. Krishna
    Sridhar, B.
    Reddy, B. V. Subba
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (28) : 4085 - 4090
  • [28] Chiral Binaphthol-Catalyzed Enantioselective Conjugate Addition of Alkenyl and Arylboronic Acids to α,β-Unsaturated Cyclic N-Sulfonyl Ketimines
    Hou, Ya-Jing
    Wang, Yang-Ling
    Chang, Junbiao
    Chai, Guo-Li
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (18): : 13137 - 13149
  • [29] B(C6F5)3-Catalyzed Reduction of Cyclic N-Sulfonyl Ketimines
    Shi, Lei
    Bao, Robert Li-Yuan
    Zheng, Limin
    Zhao, Rong
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (38) : 6550 - 6556
  • [30] Rhodium-Catalyzed Enantioselective Addition of Organoaluminum Reagents to N-Tosyl Ketimines
    Hirner, Sebastian
    Kolb, Andreas
    Westmeier, Johannes
    Gebhardt, Sandra
    Middel, Stephen
    Harms, Klaus
    von Zezschwitz, Paultheo
    ORGANIC LETTERS, 2014, 16 (11) : 3162 - 3165