Solvent-promoted catalyst-free N-formylation of amines using carbon dioxide under ambient conditions

被引：153

作者：

Lv, Hui ^{[1
,2
]}

Xing, Qi ^{[2
]}

Yue, Chengtao ^{[2
]}

Lei, Ziqiang ^{[1
]}

Li, Fuwei ^{[2
]}

机构：

[1] Northwest Normal Univ, Coll Chem & Chem Engn, Minist Educ, Key Lab Ecoenvironm Related Polymer Mat, Lanzhou 730070, Peoples R China

[2] Chinese Acad Sci, Lanzhou Inst Chem Phys, Suzhou Res Inst, Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2016年 / 52卷 / 39期

基金：

中国国家自然科学基金;

关键词：

HETEROCYCLIC CARBENE; ROOM-TEMPERATURE; REDUCTIVE FUNCTIONALIZATION; DIPHOSPHINE COMPLEX; ATM; CO2; TRANSFORMATION; CONVERSION; METHYLATION; EFFICIENT;

D O I：

10.1039/c6cc01234e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An unprecedented catalyst-free formylation of amines using CO2 and hydrosilanes was developed. The solvent plays a vital role in promoting the interaction of amines with hydrosilanes and subsequent CO2 insertion, thus facilitating the simultaneous activation of N-H and Si-H bonds. Based on relevant mechanistic studies, a plausible mechanism involving a silyl carbamate intermediate is proposed.

引用

页码：6545 / 6548

页数：4

共 50 条

[31] Nanoceria-catalyzed Highly Efficient Procedure for N-Formylation of Amines at Room Temperature under Solvent-free Conditions
Patil, Umakant B.
Singh, Abhilash S.
Nagarkar, Jayashree M.
CHEMISTRY LETTERS, 2013, 42 (05) : 524 - 526
[32] Guanidine derived ionic liquids: catalyst free medium for N-Formylation of amines
Akbari, Jafar
Hekmati, Malak
Sheykhan, Mehdi
Heydari, Akbar
ARKIVOC, 2009, : 123 - 129
[33] Carbon Dioxide Based N-Formylation of Amines Catalyzed by Fluoride and Hydroxide Anions
Hulla, Martin
Bobbink, Felix D.
Das, Shoubhik
Dyson, Paul J.
CHEMCATCHEM, 2016, 8 (21) : 3338 - 3342
[34] A very simple and highly efficient procedure for N-formylation of primary and secondary amines at room temperature under solvent-free conditions
Brahmachari, Goutam
Laskar, Sujay
TETRAHEDRON LETTERS, 2010, 51 (17) : 2319 - 2322
[35] Amino group immobilized on polyvinyl alcohol as a reusable catalyst for highly accelerated N-formylation of amines using formic acid under solvent-free condition
Rezazadeh, Soodabeh
Akhlaghinia, Batool
JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 2015, 92 (08) : 1277 - 1285
[36] N-Heterocyclic carbene supported zinc catalysed N-formylation of diverse N-H functionalities with carbon dioxide under ambient conditions
Sahoo, Sangita
Manna, Subarna
Rit, Arnab
CATALYSIS SCIENCE & TECHNOLOGY, 2023, 13 (11) : 3344 - 3350
[37] Ambient-Light-Promoted Stereospecific Synthesis of (Z)-Vinyl Thioesters under Solvent- and Catalyst-Free Conditions
Wang, Rui
Yuan, Jia-Long
Liang, Kun-Long
Hu, Ji-Yun
Fu, Qiang
Liang, Fu-Shun
JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (13): : 9597 - 9608
[38] Protic [TBD][TFA] ionic liquid as a reusable and highly efficient catalyst for N-formylation of amines using formic acid under solvent-free condition
Baghbanian, Seyed Meysam
Farhang, Maryam
JOURNAL OF MOLECULAR LIQUIDS, 2013, 183 : 45 - 49
[39] N-FORMYLATION OF CYCLIC SECONDARY-AMINES UNDER INTERPHASE CATALYSIS CONDITIONS
GOLDBERG, YS
SHIMANSKAYA, MV
ZHURNAL ORGANICHESKOI KHIMII, 1982, 18 (10): : 2036 - 2042
[40] Magnesium oxide as an efficient catalyst for CO2 fixation and N-formylation reactions under ambient conditions
Chowdhury, Arpita Hazra
Bhanja, Piyali
Salam, Noor
Bhaumik, Asim
Islam, Sk. Manirul
MOLECULAR CATALYSIS, 2018, 450 : 46 - 54

← 1 2 3 4 5 →