I2-mediated Csp2-P bond formation via tandem cyclization of o-alkynylphenyl isothiocyanates with organophosphorus esters

被引：2
|
作者：
Liu, Yang [1 ]
Wu, Wenjin [1 ]
Sang, Xiaoyan [1 ]
Xia, Yu [1 ]
Fang, Guojian [1 ]
Hao, Wenyan [1 ]
机构：
[1] Jiangxi Normal Univ, Coll Chem & Chem Engn, Nanchang 330022, Jiangxi, Peoples R China
来源：
RSC ADVANCES | 2022年 / 12卷 / 28期
关键词：
CATALYZED P-ARYLATION; RADICAL C-P; EFFICIENT SYNTHESIS; CASCADE REACTION; 6-PHOSPHORYLATED PHENANTHRIDINES; DIARYLIODONIUM SALTS; ARYLBORONIC ACIDS; COUPLING REACTION; PHOSPHINE OXIDES; H-PHOSPHONATES;
D O I：
10.1039/d2ra03072a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A novel, I-2-mediated tandem cyclization of o-alkynylphenyl isothiocyanates with organophosphorus esters has been developed under mild conditions. Different kinds of 4H-benzo[d][1,3]thiazin-2-ylphosphonate could be synthesized in moderate to excellent yields. This method has the advantages of easy access to raw materials, free-metal catalyst, simple operation, high yield and high functional group tolerance.
引用
收藏
页码：18072 / 18076
页数：5
相关论文
共 50 条
  • [31] n-Bu4NI/K2S2O8 Mediated Csp2-Csp2 Bond Cleavage - Transformylation from p-Anisaldehyde to Primary Amides
    Liu, Xiaochen
    Hee, Samual
    Sapir, Netanel G.
    Li, Alvin
    Liu, Jianbo
    Chen, Yu
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (11) : 2489 - 2494
  • [32] Tf2O-Mediated P(O)-N Bond Formation of Either P(O)-OH or P(O)-H Reagents with Multitype Amines
    Shi, Da-Wei
    Yue, Hui-Qi
    Li, Ming
    Liu, Jie
    Wang, Chang-Cheng
    Yang, Shang-Dong
    Yang, Bin
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (10): : 6729 - 6739
  • [33] Csp2-O and C-C Bond Formation via Pd-Catalyzed Coupling Reaction of 2,4-Dichloroquinazoline
    Sharma, Alka
    Luxami, Vijay
    Paul, Kamaldeep
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2016, 53 (01) : 241 - 248
  • [34] Unprecedented SnCl2•2H2O-mediated intramolecular cyclization of nitroarenes via C-N bond formation: a new entry to the synthesis of cryptotackieine and related skeletons
    Sharma, Sunil
    Kundu, Bijoy
    TETRAHEDRON LETTERS, 2008, 49 (49) : 7062 - 7065
  • [35] Formation of new C-O and C-N bonds via base promoted Csp2-Csp3 bond cleavage of α-nitro ketone
    Sarma, Manas Jyoti
    Borah, Arun Jyoti
    Rajbongshi, Kamal Krishna
    Phukan, Prodeep
    TETRAHEDRON LETTERS, 2015, 56 (50) : 7008 - 7011
  • [36] Direct Synthesis of Benzo[b]fluorenyl Thiophosphates via Tandem Cyclization of Diynols with (RO)2P(O)SH
    Du, Sha
    Jiang, Shimin
    Yang, Ruchun
    Jin, Fengyan
    Huang, Haiyang
    Tian, Wan-Fa
    Zhou, Zhao-Zhao
    Song, Xian-Rong
    Xiao, Qiang
    ORGANIC LETTERS, 2023, : 1263 - 1267
  • [37] Enantioselective Syntheses of Spiroketals via a Tandem Reaction of Cu(I)-Catalyzed Cycloetherification and Hydrogen-Bond-Induced [4+2] Cyclization
    Tian, Tian
    Li, Liqi
    Xue, Jijun
    Zhang, Jie
    Li, Ying
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (08): : 4189 - 4200
  • [38] Synthesis of 5-Amino and 3,5-Diamino Substituted 1,2,4-Thiadiazoles by I2-Mediated Oxidative N-S Bond Formation
    Wang, Bingnan
    Meng, Yinggao
    Zhou, Yiming
    Ren, Linning
    Wu, Jie
    Yu, Wenquan
    Chang, Junbiao
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (11): : 5898 - 5903
  • [39] NBS-mediated practical cyclization of N-acyl amidines to 1,2,4-oxadiazoles via oxidative N-O bond formation
    Li, Ertong
    Wang, Manman
    Wang, Zhen
    Yu, Wenquan
    Chang, Junbiao
    TETRAHEDRON, 2018, 74 (35) : 4613 - 4618
  • [40] CuI/I2-Mediated Intramolecular Oxidative Cyclization Reaction of N-(2-pyridyl)amidines by the Direct Double C-H Functionalization of a C(sp3)-H Bond
    Yi, Fengping
    Zhang, Songxing
    Zhang, Lirong
    Yi, Weiyin
    Yu, Rui
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (12) : 1808 - 1817
12345