Heterocyclic Boron Acid Catalyzed Dehydrative Amidation of Aliphatic/Aromatic Carboxylic Acids with Amines

被引：25

作者：

Pan, Bin ^{[2
]}

Huang, Ding-Min ^{[3
]}

Sun, Hao-Tian ^{[3
]}

Song, Sheng-Nan ^{[3
]}

Su, Xian-Bin ^{[1
]}

机构：

[1] Nanjing Tech Univ, Coll Chem Engn, State Key Lab Mat Oriented Chem Engn, Nanjing 210009, Peoples R China

[2] Weifang Univ Sci & Technol, Shandong Peninsula Engn Res Ctr Comprehens Brine U, Weifang 262700, Peoples R China

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 05期

关键词：

DIRECT AMIDE FORMATION; PEPTIDE-BOND FORMATION; MECHANISTIC INSIGHTS; CONDENSATION; EFFICIENT; PALLADIUM; TRANSAMIDATION; ACTIVATION; ALDEHYDES; CARBON;

D O I：

10.1021/acs.joc.2c02515

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A commercially available and versatile dehydrative amidation catalyst, featuring a thianthrene boron acid structure, has been developed. The catalyst shows high catalytic activity to both aliphatic and less reactive aromatic carboxylic acid substrates, including several bioactive or clinical molecules with a carboxylic acid group.

引用

页码：2832 / 2840

页数：9

共 50 条

[41] Boron-Catalyzed α-Amination of Carboxylic Acids
Morisawa, Takuto
Sawamura, Masaya
Shimizu, Yohei
ORGANIC LETTERS, 2019, 21 (18) : 7466 - 7469
[42] ZnO nanofluid as a structure base catalyst for chemoselective amidation of aliphatic carboxylic acids
Tamaddon, Fatemeh
Aboee, Fatemeh
Nasiri, Alireza
CATALYSIS COMMUNICATIONS, 2011, 16 (01) : 194 - 197
[43] Selective esterification of aliphatic carboxylic acids in the presence of aromatic carboxylic acids over monoammonium salt of 12-tungstophosphoric acid
Giri, BY
Devi, BLAP
Gangadhar, KN
Rao, KN
Lingaiah, N
Sai Prasad, PS
Prasad, RBN
SYNTHETIC COMMUNICATIONS, 2006, 36 (01) : 7 - 11
[44] N-Heterocyclic Carbene-Catalyzed Oxidative Amidation of Aldehydes with Amines
Alanthadka, Anitha
Maheswari, C. Uma
ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (06) : 1199 - 1203
[45] LOW-TEMPERATURE AMIDATION OF CARBOXYLIC-ACIDS BY AROMATIC CARBODIIMIDES
VOVK, MV
DOROKHOV, VI
SAMARAI, LI
ZHURNAL ORGANICHESKOI KHIMII, 1987, 23 (06): : 1339 - 1340
[46] REACTIONS OF CARBOXYLIC-ACIDS WITH AROMATIC-AMINES
MASLOSH, VZ
CHASNYK, OF
KUDYUKOV, YP
IGNATKINA, TR
IZVESTIYA VYSSHIKH UCHEBNYKH ZAVEDENII KHIMIYA I KHIMICHESKAYA TEKHNOLOGIYA, 1983, 26 (07): : 794 - 798
[47] Dehydrative esterification of carboxylic acids with alcohols catalyzed by polymer-supported sulfonic acids in water
Manabe, K
Kobayashi, S
ADVANCED SYNTHESIS & CATALYSIS, 2002, 344 (3-4) : 270 - 273
[48] CuH-Catalyzed Asymmetric Reductive Amidation of α,β-Unsaturated Carboxylic Acids
Link, Achim
Zhou, Yujing
Buchwald, Stephen L.
ORGANIC LETTERS, 2020, 22 (14) : 5666 - 5670
[49] REACTION OF CARBOXYLIC-ACID HYDRAZIDES WITH PHOSPHORUS PENTACHLORIDE .3. HYDRAZIDES OF ALIPHATIC AND HETEROCYCLIC CARBOXYLIC-ACIDS
YAGUPOLSKII, LM
MATYUSHE.GI
MIKHAILO.VS
ZHURNAL ORGANICHESKOI KHIMII, 1972, 8 (04): : 838 - +
[50] Multivalent metal salts as versatile catalysts for the amidation of long-chain aliphatic acids with aliphatic amines
Terada, Yuji
Leda, Noboru
Komura, Kenichi
Sugi, Yoshihiro
SYNTHESIS-STUTTGART, 2008, (15): : 2318 - 2320

← 1 2 3 4 5 →