Synthesis of N-Aryl Carbamates from Aryl(TMP)iodonium Salts via C-N Coupling

被引：1

作者：

Hatton, Joseph ^{[1
]}

Stuart, David R. ^{[1
]}

机构：

[1] Portland State Univ, Dept Chem, Portland, OR 97201 USA

来源：

ORGANIC LETTERS | 2025年

基金：

美国国家科学基金会;

关键词：

ONE-POT SYNTHESIS; HIGHLY EFFICIENT; CARBON-DIOXIDE; DIARYLIODONIUM SALTS; BOND FORMATION; IONIC LIQUID; ARYLATION; METAL; OXAZOLIDINONES; AMIDES;

D O I：

10.1021/acs.orglett.4c04582

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Modular C-N coupling is a desirable way to construct N-aryl carbamates, which are privileged scaffolds in active pharmaceutical ingredients. However, there are no broadly applicable metal-free methods for theN-arylation of carbamates. Herein, we describe a metal-free approach that uses aryl(TMP)iodonium salts as arylation reagents for cyclic carbamates by exploiting the metal-like reactivity of iodine(III). The scope includes 25 examples, including 17 different aryl(TMP)iodonium salts and 9 different carbamates, in yields ranging between 55 and 97% (75% avg).

引用

页数：6

共 50 条

[21] A facile synthesis of N-aryl aziridines
Sriraghavan, K
Ramakrishnan, VT
SYNTHETIC COMMUNICATIONS, 2001, 31 (07) : 1105 - 1121
[22] N-Aryl and N-Alkyl Carbamates from 1 Atmosphere of CO2
Takeuchi, Katsuhiko
Chen, Ming-Yu
Yuan, Hao-Yu
Koizumi, Hiroki
Matsumoto, Kazuhiro
Fukaya, Norihisa
Choe, Yoong-Kee
Shigeyasu, Shinji
Matsumoto, Seiji
Hamura, Satoshi
Choi, Jun-Chul
CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (72) : 18066 - 18073
[23] Synthesis of Some N-Aryl α-Amino Acids Using Diaryliodonium Salts
McKerrow, Jason D.
Al-Rawi, Jasim M.
Brooks, Peter
ASIAN JOURNAL OF CHEMISTRY, 2012, 24 (03) : 1227 - 1236
[24] Asymmetric synthesis of N-aryl sulfinamides: copper(I)-catalyzed coupling of sulfinamides with aryl iodides via kinetic resolution
Liu, Yangyuan
Wang, Zesheng
Guo, Bin
Cai, Qian
TETRAHEDRON LETTERS, 2016, 57 (22) : 2379 - 2381
[25] Examining Heterodimerization by Aryl C-N Coupling in Dynemicin Biosynthesis
Pal, Paramita
Alley, Jamie R.
Townsend, Craig A.
ACS CHEMICAL BIOLOGY, 2023, 18 (02) : 304 - 314
[26] Synthesis of substituted benzimidazoles via tosylation of N-aryl amidoxime
Yamamoto, Yuhei
Tsuritam, Takayuki
Mase, Toshiaki
TETRAHEDRON LETTERS, 2008, 49 (05) : 876 - 878
[27] SYNTHESIS OF 4-DIALKYLAMINOQUINAZOLINES FROM THE REACTION OF N-ARYL NITRILIUM SALTS WITH DIALKYLCYANAMIDES
ALTALIB, M
JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG, 1993, 335 (08): : 711 - 713
[28] New strategy for the synthesis of N-aryl pyrroles: Cu-catalyzed C-N cross-coupling reaction of trans-4-hydroxy-L-proline with aryl halides
Reddy, V. Prakash
Kumar, A. Vijay
Rao, K. Rama
TETRAHEDRON LETTERS, 2011, 52 (07) : 777 - 780
[29] Synthesis and Biological Activities of Some Novel N-Aryl Sulfonyl Trytophanates and N-Aryl Sulfonyl Glutamates
Li Wen-Ming
Tan Hai-Zhong
Wang Jian-Guo
Li Yong-Hong
Li Zheng-Ming
CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2009, 30 (04): : 728 - 730
[30] Reductive Transamination of Pyridinium Salts to N-Aryl Piperidines
Chen, Zhenyu
Song, Geyang
Qi, Leiming
Gunasekar, Ramachandran
Aissa, Christophe
Robertson, Craig
Steiner, Alexander
Xue, Dong
Xiao, Jianliang
JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (13): : 9352 - 9359

← 1 2 3 4 5 →