Visible photons for the regioselective nucleophilic ring opening of epoxides

被引：1

作者：

Bernardoni, Beatrice ^{[1
]}

Di Terlizzi, Lorenzo ^{[1
]}

Galathri, Eirini M. ^{[2
]}

Kokotos, Christoforos G. ^{[2
]}

Fagnoni, Maurizio ^{[1
]}

Protti, Stefano ^{[1
]}

机构：

[1] Univ Pavia, Dept Chem, PhotoGreen Lab, Viale Taramelli 12, I-27100 Pavia, Italy

[2] Natl & Kapodistrian Univ Athens, Dept Chem, Lab Organ Chem, Athens 15771, Greece

来源：

GREEN CHEMISTRY | 2024年 / 26卷 / 18期

关键词：

BETA-HYDROXY; EFFICIENT CATALYST; PHOTOBASE GENERATORS; ACID CATALYST; OXIRANES; THIIRANES; CYCLODEXTRIN; WATER; CONVERSION; AZIRIDINES;

D O I：

10.1039/d4gc02612h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Arylazo sulfones were used as Photoacid Generators (PAGs) for the visible-light photorelease of strong sulfonic acids to promote the ring opening of epoxides in benign media (DMC/water mixtures) or under neat conditions. Water, alcohols, azide and thiocyanate anions, as well as electron-rich aromatics were used in the role of the nucleophile. The resulting 1,2-disubstituted adducts were formed mostly in >99% yield in a high regioselective fashion.

引用

页码：9833 / 9839

页数：7

共 50 条

[41] Regioselective ring opening of oxiranes to halohydrins with tetrabutylammonium halide in water in the presence of β-cyclodextrin
Surendra, K
Krishnaveni, NS
Kumar, VP
Nageswar, YVD
Rao, KR
LETTERS IN ORGANIC CHEMISTRY, 2005, 2 (07) : 652 - 658
[42] Catalyst-Free Efficient Regioselective Ring Opening of Oxiranes with Thioacids in Water
Halimehjani, Azim Ziyaei
Jalali, Aazam
Khalesi, Maryam
Ashouri, Akram
Marjani, Katayoun
SYNTHETIC COMMUNICATIONS, 2011, 41 (11) : 1638 - 1643
[43] Regioselective ring-opening of aziridines with potassium thiocyanate in the presence of β-cyclodextrin in water
Reddy, MS
Narender, M
Nageswar, YVD
Rao, KR
TETRAHEDRON LETTERS, 2005, 46 (38) : 6437 - 6439
[44] Regioselectivity Control of the Ring Opening of Epoxides With Sodium Azide in a Microreactor
Munirathinam, Rajesh
Joe, Daejune
Huskens, Jurriaan
Verboom, Willem
JOURNAL OF FLOW CHEMISTRY, 2012, 2 (04) : 129 - +
[45] Gallium trichloride-promoted highly regioselective ring opening of epoxides with NH4SCN and NaN3 in water
Chen, Xian
Wu, Huayue
Xu, Rong
Liu, Miaochang
Ding, Jinchang
Su, Weike
SYNTHETIC COMMUNICATIONS, 2008, 38 (11) : 1855 - 1865
[46] An efficient catalyst for ring opening of epoxides with phenol and thiophenol under solvent-free conditions
Lu, Hong-fei
Zhou, Jun-tao
Cheng, He-long
Sun, Lei-lei
Yang, Fei-fei
Wu, Run-ze
Gao, Yu-hua
Luo, Zhi-bin
TETRAHEDRON, 2013, 69 (52) : 11174 - 11184
[47] LiOH-Catalyzed Simple Ring Opening of Epoxides Under Solvent-Free Conditions
Azizi, Najmedin
Khajeh-Amiri, Alireza
Ghafuri, Hossein
Bolourtchian, Mohammad
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2010, 185 (07) : 1550 - 1557
[48] Odorless regioselctive ring opening of epoxides with S-alkylisothiouronium salts as masked thiols in water
Panchadhayee, Rajib
Misra, Anup Kumar
ARKIVOC, 2009, : 298 - 307
[49] Cobalt Catalyst Determines Regioselectivity in Ring Opening of Epoxides with Aryl Halides
Potrzasaj, Aleksandra
Musiejuk, Mateusz
Chaladaj, Wojciech
Giedyk, Maciej
Gryko, Dorota
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (25) : 9368 - 9376
[50] Highly efficient deep eutectic solvent catalyzed ring opening of epoxides
Azizi, Najmadin
Batebi, Elham
CATALYSIS SCIENCE & TECHNOLOGY, 2012, 2 (12) : 2445 - 2448

← 1 2 3 4 5 →