Thiamine hydrochloride as a recyclable organocatalyst for the efficient and chemoselective N-tert-butyloxycarbonylation of amines

被引：5
|
作者：
Ingale, Ajit P. [1 ]
Garad, Dnyaneshwar N. [2 ]
Ukale, Dattatraya [3 ]
Thorat, Nitin M. [4 ]
Shinde, Sandeep, V [5 ]
机构：
[1] Savitribai Phule Pune Univ, Dada Patil Coll, Dept Chem, Ahmednagar, Maharashtra, India
[2] Natl Univ Ireland Galway, Sch Chem, Galway, Ireland
[3] Univ Oxford, Dept Chem, Oxford, England
[4] Savitribai Phule Pune Univ, Maharaja Jivajirao Shinde Coll, Dept Chem, Shrigonda, Ahmednagar, India
[5] Swami Ramanand Teerth Marathwada Univ, Pratibha Niketan Coll, Dept Chem, Nanded, India
来源：
SYNTHETIC COMMUNICATIONS | 2021年 / 51卷 / 24期
关键词：
Chemoselective; eco-friendly; N-tert butyloxycarbonylation; recyclable; thiamin hydrochloride; ONE-POT SYNTHESIS; CATALYZED BOC PROTECTION; HIGHLY EFFICIENT; IONIC LIQUID; BUTYL DICARBONATE; REUSABLE CATALYST; ARYL AMINES; ACID; BUTOXYCARBONYLATION; MILD;
D O I：
10.1080/00397911.2021.1994998
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Thiamin hydrochloride promoted highly efficient and ecofriendly approach has been described for the chemoselective N-tert-butyloxycarbonylation of amines under solvent-free conditions at ambient temperature. The demonstrated approach has been applicable for the N-Boc protection of variety of aliphatic, aryl, heteroaryl amines. The chemoselective protection of amino group occurs in chiral amines and amino alcohol without racemization in high yield. Thiamin hydrochloride is stable, economical, easy to handle and environmentally friendly.
引用
收藏
页码：3791 / 3804
页数：14
相关论文
共 50 条
  • [1] Chemoselective N-tert-butyloxycarbonylation of amines in glycerol
    Ingale, Ajit P.
    More, Vishal K.
    Gangarde, Uddhav S.
    Shinde, Sandeep V.
    NEW JOURNAL OF CHEMISTRY, 2018, 42 (12) : 10142 - 10147
  • [2] Catalyst-free chemoselective N-tert-butyloxycarbonylation of amines in water
    Chankeshwara, Sunay V.
    Chakraborti, Asit K.
    ORGANIC LETTERS, 2006, 8 (15) : 3259 - 3262
  • [3] Ultrasound promoted environmentally benign, highly efficient, and chemoselective N-tert-butyloxycarbonylation of amines by reusable sulfated polyborate
    Pise, Ashok A.
    Ingale, Ajit P.
    Dalvi, Navnath R.
    SYNTHETIC COMMUNICATIONS, 2021, 51 (24) : 3768 - 3780
  • [4] NBS and Br3CCOCBr3 as highly efficient catalysts for the chemoselective N-tert-butyloxycarbonylation of amines
    Chantarasriwong, Oraphin
    Jiangchareon, Banphot
    Putra, Christian Kurnia
    Suwankrua, Winai
    Chavasiri, Warinthorn
    TETRAHEDRON LETTERS, 2016, 57 (43) : 4807 - 4811
  • [5] Nanoceria as an efficient and green catalyst for the chemoselective N-tert-butyloxycarbonylation of amines under the solvent-free conditions
    Ingale, Ajit P.
    Ukale, Dattatraya
    Garad, Dnyaneshwar N.
    Shinde, Sandeep V.
    SYNTHETIC COMMUNICATIONS, 2021, 51 (11) : 1656 - 1668
  • [6] Microwave assisted mild, rapid, solvent-less, and catalyst-free chemoselective N-tert-butyloxycarbonylation of amines
    Dighe, Satish N.
    Jadhav, Hemant R.
    TETRAHEDRON LETTERS, 2012, 53 (43) : 5803 - 5806
  • [7] Sulfated tungstate: A highly efficient, recyclable and ecofriendly catalyst for chemoselective N-tert butyloxycarbonylation of amines under the solvent-free conditions
    Ingale, Ajit P.
    Shinde, Sandeep, V
    Thorat, Nitin M.
    SYNTHETIC COMMUNICATIONS, 2021, 51 (16) : 2528 - 2543
  • [8] N-TERT-BUTYLOXYCARBONYLATION OF AMINO-ACIDS BY TERT-BUTYLDINITROPHENYLCARBONATE
    POZDNEV, VF
    KHIMIYA PRIRODNYKH SOEDINENII, 1975, (03): : 437 - 438
  • [9] Copper nanoparticles catalyzed N-H functionalization: An efficient solvent-free N-tert-butyloxycarbonylation strategy
    Deb, Barnali
    Debnath, Sudipto
    Deb, Anindita
    Maiti, Dilip K.
    Majumdar, Swapan
    TETRAHEDRON LETTERS, 2017, 58 (07) : 629 - 633
  • [10] Sustainable Route Toward N-Boc Amines: AuCl3/CuI-Catalyzed N-tert-butyloxycarbonylation of Amines at Room Temperature
    Cao, Yanwei
    Huang, Yang
    He, Lin
    CHEMSUSCHEM, 2022, 15 (04)
12345