Mechanochemical Aliphatic Iodination (and Bromination) by Cascaded Cyclization

被引:7
作者
Bal, Ankita [1 ]
Dinda, Tarun Kumar [1 ]
Mal, Prasenjit [1 ]
机构
[1] OCC Homi Bhabha Natl Inst, Natl Inst Sci Educ & Res NISER Bhubaneswar, Sch Chem Sci, PO Bhimpur Padanpur,Via Jatni, Bhubaneswar 752050, Odisha, India
关键词
Aliphatic iodination; Bifunctional reagents; Cascaded cyclization; Iodonium cation; Mechanochemistry; OXIDATIVE CYCLIZATION; EFFICIENT; SYSTEM; HETEROCYCLES; ROUTE; FORCE; TBHP;
D O I
10.1002/ajoc.202200046
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Aliphatic iodination via mechanochemistry is a mammoth challenge due to the high polarizability and weak electrophilicity of iodonium cation (I+), and low bond dissociation energy of carbon iodine bond. Herein, the synthesis is demonstrated of oxazoline derivatives from N-allyl benzamides via mechanochemical cascaded cyclization and halogenation using N-iodo- and N-bromosuccinimides, respectively, as bifunctional reagents.
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页数:4
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共 48 条
[1]   Stereoselective Oxidative Cyclization of N-Allyl Benzamides to Oxaz(ol)ines [J].
Abazid, Ayham H. ;
Hollwedel, Tom-Niklas ;
Nachtsheim, Boris J. .
ORGANIC LETTERS, 2021, 23 (13) :5076-5080
[2]   Mechanochemical synthesis of small organic molecules [J].
Achar, Tapas Kumar ;
Bose, Anima ;
Mal, Prasenjit .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2017, 13 :1907-1931
[3]   PIDA-I2 mediated direct vicinal difunctionalization of olefins: iodoazidation, iodoetherification and iodoacyloxylation [J].
Achar, Tapas Kumar ;
Maiti, Saikat ;
Mal, Prasenjit .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (20) :4654-4663
[4]   Transformation of Contact-Explosives Primary Amines and Iodine(III) into a Successful Chemical Reaction under Solvent-Free Ball Milling Conditions [J].
Achar, Tapas Kumar ;
Mal, Prasenjit .
ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (18) :3977-3985
[5]   Sustainability Assessment of Mechanochemistry by Using the Twelve Principles of Green Chemistry [J].
Ardila-Fierro, Karen J. ;
Hernandez, Jose G. .
CHEMSUSCHEM, 2021, 14 (10) :2145-2162
[6]   Aliphatic C-H Bond Iodination by a N-lodoamide and Isolation of an Elusive N-Amidyl Radical [J].
Artaryan, Alexander ;
Mardyukov, Artur ;
kulbitski, Kseniya ;
Avigdori, Idan ;
Nisnevich, Gennady A. ;
Schreiner, Peter R. ;
Gandelman, Mark .
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (14) :7093-7100
[7]   Novel Methodologies for Chemical Activation in Organic Synthesis under Solvent-Free Reaction Conditions [J].
Avila-Ortiz, Claudia Gabriela ;
Juaristi, Eusebio .
MOLECULES, 2020, 25 (16)
[8]   Mechanochemical Aliphatic Iodination (and Bromination) by Cascaded Cyclization [J].
Bal, Ankita ;
Dinda, Tarun Kumar ;
Mal, Prasenjit .
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (03)
[9]   Strategies to Control Hypervalent Iodine - Primary Amine Reactions [J].
Bal, Ankita ;
Maiti, Saikat ;
Mal, Prasenjit .
CHEMISTRY-AN ASIAN JOURNAL, 2020, 15 (06) :624-635
[10]   Mechanochemical-Cascaded C-N Cross-Coupling and Halogenation Using N-Bromo- and N-Chlorosuccinimide as Bifunctional Reagents [J].
Bera, Shyamal Kanti ;
Mal, Prasenjit .
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (20) :14144-14159