Synthesis of Unsymmetrical Diorganyl Chalcogenides under Greener Conditions: Use of an Iodine/DMSO System, Solvent‐ and Metal‐Free Approach

Advanced Synthesis and Catalysis - Tập 357 Số 7 - Trang 1446-1452 - 2015
Sumbal Saba1, Jamal Rafique1, Antônio L. Braga1
1Departamento de Química, Universidade Federal de Santa Catarina, Florianopolis 88040-900, SC – Brazil,

Tóm tắt

AbstractHerein, we report a greener iodine‐catalyzed protocol to access different types of unsymmetrical diorganyl chalcogenides. This new approach works in the absence of solvent and metal. The desired products were obtained in good to excellent yields using one equivalent of arylboronic acids, half an equivalent of various diorganyl dichalcogenides, iodine (10 mol%) as a catalyst and 2 equivalents of dimethyl sulfoxide (DMSO; as oxidant), with a reaction time of 10 min under microwave irradiation.magnified image

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Tài liệu tham khảo

 

10.1039/C4GC00874J

10.1021/jo500094t

10.1039/c2gc16541d

10.1039/c2gc16427b

10.1021/jo0007433

 

10.1021/cr100214d

10.1021/cr0505730

10.1021/cr8004394

10.1021/ar100059g

10.1021/cr0406559

 

2014, The Chemistry of Organic Selenium and Tellurium Compounds

2013, Handbook of Chalcogen Chemistry: New Perspectives in Sulfur, Selenium and Tellurium

2011, Organoselenium Chemistry: Synthesis and Reactions

 

10.1039/c1dt11022e

10.1016/j.tet.2005.09.044

10.1021/jo0261707

10.1021/jo00012a006

10.1016/j.tet.2012.08.004

10.1021/ol202800k

10.1039/c0dt00561d

 

10.1016/j.tetlet.2012.03.076

10.1002/1521-3757(20021115)114:22<4476::AID-ANGE4476>3.0.CO;2-S

10.1002/1521-3773(20021115)41:22<4300::AID-ANIE4300>3.0.CO;2-V

 

10.1021/jo100139u

10.1002/ange.200601872

10.1002/anie.200601872

10.1016/j.tetlet.2004.03.154

 

Braga A. L., 2013, The Chemistry of Organic Selenium and Tellurium Compounds, 989

10.1039/c0ob00086h

10.1021/cr000426w

10.1097/00001813-200302000-00009

10.1021/jm030916r

 

10.1021/ja4028583

10.1021/cm102395v

10.1021/jp0370674

10.1021/ja00166a019

 

10.1021/cr100108k

10.1002/adsc.201400305

2011, Boronic Acids: Preparation and Applications in Organic Synthesis Medicine and Materials

 

1991, Comprehensive Organic Synthesis

10.1002/9783527619535.ch2

Krief A., 1995, ComprehensiveOrganometallic Chemistry II

 

10.1021/jo900385d

10.1021/ol990233z

10.1021/ol047996t

10.1021/ja00115a033

10.1021/jo040184q

 

10.1590/S0103-50532009000500025

10.1016/j.tet.2014.01.030

10.1021/jo062131

10.1016/j.tetlet.2009.09.052

10.1039/c2gc35328h

10.1002/adsc.200900095

10.1039/b914533h

10.1021/jo060690a

 

10.1021/jo502274t

10.1039/c3ob41601a

10.1021/jo302480j

 

10.1021/ol501029w

10.1039/c2gc35337g

10.1021/ol5027393

10.1002/adsc.201300773

10.1021/jo5000779

 

10.1039/C4RA10490K

10.1002/ajoc.201300092

10.1039/c002648d

 

10.1002/adsc.201400305

10.1002/adsc.201300773

 

10.1021/ja00763a003

10.1139/v83-331