Access to Nitriles from Aldehydes Mediated by an Oxoammonium Salt

被引：99

作者：

Kelly, Christopher B. ^{[1
]}

Lambert, Kyle M. ^{[1
]}

Mercadante, Michael A. ^{[1
]}

Ovian, John M. ^{[1
]}

Bailey, William F. ^{[1
]}

Leadbeater, Nicholas E. ^{[1
,2
]}

机构：

[1] Univ Connecticut, Dept Chem, Storrs, CT 06269 USA

[2] Univ Connecticut, Ctr Hlth, Dept Community Med & Hlth Care, Exchange, Farmington, CT 06030 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 14期

基金：

美国国家科学基金会;

关键词：

aldehydes; cyanides; oxidation; reaction mechanisms; synthetic methods; PRIMARY AMINES; OXIDATIVE SYNTHESIS; AEROBIC OXIDATION; PRIMARY ALCOHOLS; AQUEOUS AMMONIA; PRIMARY AMIDES; EFFICIENT; CONVERSION; DEHYDRATION; ALDOXIMES;

D O I：

10.1002/anie.201412256

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A scalable, high yielding, rapid route to access an array of nitriles from aldehydes mediated by an oxoammonium salt (4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate) and hexamethyldisilazane (HMDS) as an ammonia surrogate has been developed. The reaction likely involves two distinct chemical transformations: reversible silyl-imine formation between HMDS and an aldehyde, followed by oxidation mediated by the oxoammonium salt and desilylation to furnish a nitrile. The spent oxidant can be easily recovered and used to regenerate the oxoammonium salt oxidant.

引用

页码：4241 / 4245

页数：5

共 50 条

[1] Oxoammonium salt-mediated oxidative nitriles synthesis from aldehydes with ammonium acetate
Kim, Myeong Jin
Mun, Junyoung
Kim, Jinho
TETRAHEDRON LETTERS, 2017, 58 (50) : 4695 - 4698
[2] Oxidation of Aldehydes to Nitriles with an Oxoammonium Salt: Preparation of Piperonylonitrile
Kaetzel, Nathaniel D.
Lambert, Kyle M.
Kelly, Christopher B.
ORGANIC SYNTHESES, 2020, 97 : 294 - +
[3] Combining Oxoammonium Cation Mediated Oxidation and Photoredox Catalysis for the Conversion of Aldehydes into Nitriles
Nandi, Jyoti
Witko, Mason L.
Leadbeater, Nicholas E.
SYNLETT, 2018, 29 (16) : 2185 - 2190
[4] Oxoammonium salt oxidations of aldehydes in the presence of pyridine
Bartelson, Ashley L.
Bobbin, James M.
Bailey, William F.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238
[5] Oxidative Esterification of Aldehydes Using a Recyclable Oxoammonium Salt
Kelly, Christopher B.
Mercadante, Michael A.
Wiles, Rebecca J.
Leadbeater, Nicholas E.
ORGANIC LETTERS, 2013, 15 (09) : 2222 - 2225
[6] Oxoammonium salt oxidation of alcohols to aldehydes and carboxylic acids
Blanck, Nyle B.
Bobbitt, James M.
Bailey, William F.
Pradhan, Priya P.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
[7] Selective Oxoammonium Salt Oxidations of Alcohols to Aldehydes and Aldehydes to Carboxylic Acids
Qiu, Joseph C.
Pradhan, Priya P.
Blanck, Nyle B.
Bobbitt, James M.
Bailey, William F.
ORGANIC LETTERS, 2012, 14 (01) : 350 - 353
[8] Facile Oxidation of Primary Amines to Nitriles Using an Oxoammonium Salt
Lambert, Kyle M.
Bobbitt, James M.
Eldirany, Sherif A.
Wiberg, Kenneth B.
Bailey, William F.
ORGANIC LETTERS, 2014, 16 (24) : 6484 - 6487
[9] Access to nitriles mediated by Bobbitt's salt, an environmentally benign and recyclable oxidant
Lambert, Kyle
Eldirany, Sherif
Bailey, William
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250
[10] Oxoammonium Salt-Mediated Vicinal Oxyazidation of Alkenes with NaN3: Access to β-Aminooxy Azides
Chen, Fei
Tang, Yu-Ting
Li, Xin-Ru
Duan, Yan-Yan
Chen, Chao-Xing
Zheng, Yang
ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (22) : 5079 - 5084

← 1 2 3 4 5 →