Rh(III)-Catalyzed C-H Annulation of Sulfoxonium Ylides and 1,3-Diynes: A Rapid Access to Alkynyl-1-Naphthol Derivatives

被引：3

作者：

Kumar, Sanjeev ^{[1
]}

Borkar, Vaishnavi ^{[1
]}

Nunewar, Saiprasad ^{[1
]}

Yadav, Shashank ^{[1
]}

Kanchupalli, Vinaykumar ^{[1
]}

机构：

[1] Natl Inst Pharmaceut Educ & Res NIPER, Dept Proc Chem, Hyderabad 500037, Telangana, India

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2023年 / 18卷 / 08期

关键词：

1; 3-diynes; 4+2]-annulations; Bisannulations; C-H Functionalizations; Sulfoxonium ylides; OXIDATIVE ANNULATION; ACTIVATION; 1-NAPHTHOLS; FUNCTIONALIZATION; ANTIBACTERIAL; INHIBITORS; NAPHTHOLS; CANCER;

D O I：

10.1002/asia.202201201

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An effective redox-neutral strategy to synthesize aryl/alkynyl and alkyl/alkynyl substituted 1-naphthol derivatives has been efficaciously developed by Rh(III)-catalyzed [4+2]-annulation of sulfoxonium ylides and 1,3-diynes with excellent regio- and chemoselectivity. Subsequently, the same strategy was extended to furnish various unsymmetrical binaphthol motifs in one-pot manner. Interestingly, the TMS-derived 1,3-diyne predominantly delivered the 3-alkynyl-1-naphthol via desilylation pathway. The salient features such as traceless directing group, broad substrate scope, good functional group tolerance, and operationally simple conditions made the present protocol more valuable and appealing.

引用

页数：6

共 50 条

[21] Synthesis of 1-Aminoisoquinolines via Rh(III)-Catalyzed C-H Cascade Annulation of Benzamidines with Iodonium Ylides
Li, He
Wu, Baoheng
Chen, Tao
Yang, Shuai
Li, Wangze
Cao, Shunling
Du, Zhishuang
Lu, Ye
Xu, Ning
Jin, Xinxin
Yu, Jiaqi
Liu, Jinglin
ORGANIC LETTERS, 2025,
[22] Rh-Catalyzed C-H Activation/Annulation of Enaminones and Cyclic 1,3-Dicarbonyl Compounds: An Access to Isocoumarins
Wang, Qian
Li, Ying
Sun, Jina
Chen, Shiyu
Li, Hui
Zhou, Yu
Li, Jian
Liu, Hong
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (09) : 5348 - 5358
[23] Rhodium(III)-Catalyzed [4+2] Annulation via C-H Activation: Synthesis of Multi-Substituted Naphthalenone Sulfoxonium Ylides
Song, Xiaohan
Han, Xu
Zhang, Rui
Liu, Hong
Wang, Jiang
MOLECULES, 2019, 24 (10):
[24] Rh(III)-catalyzed [4+1]-annulation of azobenzenes with α- carbonyl sulfoxonium ylides toward 3-acyl-(2H)-indazoles
Zhu, Jiawei
Sun, Song
Cheng, Jiang
TETRAHEDRON LETTERS, 2018, 59 (23) : 2284 - 2287
[25] Rh(III) Catalyzed Redox-Neutral C-H Activation/[5+2] Annulation of Aroyl Hydrazides and Sulfoxonium Ylides: Synthesis of Benzodiazepinones
Ganesh, PothapragadaS. K. Prabhakar
Muthuraja, Perumal
Gopinath, Purushothaman
ORGANIC LETTERS, 2023, 25 (46) : 8361 - 8366
[26] Rhodium(III)-Catalyzed Synthesis of CF3-1H-benzo[de][1,8]naphthyridines via C-H Activation/Annulation of Benzimidates and CF3-Imidoyl Sulfoxonium Ylides
Wen Si
Ding Yuhao
Tian Qingyu
Ge Jin
Cheng Guolin
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (01) : 291 - 300
[27] Rh(iii)-catalyzed C-H/C-C bond annulation of enaminones with iodonium ylides to form isocoumarins
Yang, Zi
Liu, Chaoshui
Lei, Jieni
Zhou, Yi
Gao, Xiaohui
Li, Yaqian
CHEMICAL COMMUNICATIONS, 2022, 58 (97) : 13483 - 13486
[28] Redox-neutral access to isoquinolines via cobalt(III)-catalyzed C-H acylmethylation/cyclization of benzimidates with sulfoxonium ylides
Li, Min
Xia, Zhen
Tang, Lixing
Zhang, Bensong
Yan, Fupeng
Jiao, Yukun
Xiang, Shiqi
Zhang, Shiyu
Tan, Ze
Yu, Lin
TETRAHEDRON LETTERS, 2024, 146
[29] Lossen rearrangement by Rh(iii)-catalyzed C-H activation/annulation of aryl hydroxamates with alkynes: access to quinolone-containing amino acid derivatives
Petropavlovskikh, Dmitry A.
Vorobyeva, Daria V.
Godovikov, Ivan A.
Nefedov, Sergey E.
Filippov, Oleg A.
Osipov, Sergey N.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (43) : 9421 - 9426
[30] Maleimide-Controlled Formation of Indanonylpyrrolinediones and Spiroindanonylpyrrolinediones via Rh(III)-Catalyzed C-H Activation of Sulfoxonium Ylides
Muthuraja, Perumal
Akhtar, Muhammad Saeed
Gopinath, Purushothaman
Lee, Yong Rok
ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (24) : 4595 - 4602

← 1 2 3 4 5 →