A simple and eco-sustainable method for the O-Boc protection/deprotection of various phenolic structures under water-mediated/catalyst-free conditions

References

• Greene TW , Wuts PGM . Protecting groups in organic synthesis. , 4th ed . New York (NY) : Wiley ; 2007 .
   Google Scholar
• Kocienski PJ . Protecting groups. , 3rd ed . New York (NY) : George Thieme Verlag ; 2004 .
   Google Scholar
• Ouchi H , Saito Y , Yamamoto Y , Takahata . H . 1-tert-Butoxy-2-tert-butoxycarbonyl-1,2-dihydroisoquinoline: A Novel and Chemoselective tert-Butoxycarbonylation reagent . Org. Lett . 2002 ; 4 : 585 – 587 . doi: 10.1021/ol017183u
   PubMed Web of Science ®Google Scholar
• Saito Y , Ouchi H , Takahata H . A novel tert-butoxycarbonylation reagent: 1-tert-butoxy-2-tert-butoxycarbonyl-1,2-dihydroisoquinoline (BBDI) . Tetrahedron . 2006 ; 62 : 11599 – 11607 .
   Web of Science ®Google Scholar
• Shivari R , Chakraborti AK . Zinc perchlorate hexahydrate [Zn(ClO4)2.6H2O] as acylation catalyst for poor nucleophilic phenols, alcohols and amines: Scope and limitations . J. Mol. Catal. A: Chem . 2007 ; 264 : 208 – 213 . doi: 10.1016/j.molcata.2006.09.015
   Google Scholar
• Chakraborti , AK , Shivari R. J . Org. Chem . 2006 ; 71 : 5785 – 5788 . doi: 10.1021/jo0605142
   PubMed Web of Science ®Google Scholar
• Houlihan F , Bouchard F , Fichet JM , Wilson CG . Phase transfer catalysis in the tert-butyloxycarbonylation of alcohols, phenols, enols, and thiols with di-tert-butyl dicarbonate . Can. J. Chem . 1985 ; 63 : 153 – 156 . doi: 10.1139/v85-025
   Web of Science ®Google Scholar
• Basel Y , Hassner A . Di-tert-butyl Dicarbonate and 4-(Dimethylamino)pyridine revisited. Their reactions with amines and alcohols . J. Org. Chem . 2000 ; 65 : 6368 – 6380 . doi: 10.1021/jo000257f
   PubMed Web of Science ®Google Scholar
• Suryakiran N , Prabhakar P , Venkateswarlu Y . ChemInform Abstract: Facile tert-Butoxycarbonylation of Alcohols, Phenols, and Amines Using BiCl3 as a Mild and Efficient Catalyst . Synth. Commun . 2008 ; 38 : 177 – 185 . doi: 10.1080/00397910701749617
   Web of Science ®Google Scholar
• Bartoli G , Bosco M , Carlone A , Dalpozzo R , Locatelli M , Melchiorre P , Palazzi P , Sambri L . Synlett 2006 ; 2104 – 2108 . doi: 10.1055/s-2006-949609
   Google Scholar
• Singh SJ , Jayaram RV . Tetrahedron Lett . 2008 ; 49 : 4249 – 4256 . doi: 10.1016/j.tetlet.2008.04.149
   Web of Science ®Google Scholar
• Saito Y , Yoshimura Y , Takahata H . Chemoselective O-tert-butoxycarbonylation of phenols using 6,7-dimethoxyisoquinoline as a novel organocatalyst . Tetrahedron Lett . 2010 : 51 ; 6915 – 6917 . doi: 10.1016/j.tetlet.2010.10.114
   Google Scholar
• Hansen MM , Riggs JR . A Novel Protecting Group for Hindered Phenols . Tetrahedron Lett . 1998 ; 39 : 2705 – 2706 . doi: 10.1016/S0040-4039(98)00411-0
   Web of Science ®Google Scholar
• Nakamura K , Nakajima T , Kayahara H , Nomura E , Taniguchi H . Base-labile tert-butoxycarbonyl (Boc) group on phenols . Tetrahedron Lett . 2004 ; 45 : 495 – 499 . doi: 10.1016/j.tetlet.2003.11.008
   Google Scholar
• Chankeshwara SV , Chebolu R , Chakraborti AK . Organocatalytic Methods for Chemoselective O-tert-Butoxycarbonylation of Phenols and Their Regeneration from the O-t-Boc Derivatives . J. Org. Chem . 2008 ; 73 : 8615 – 8618 . doi: 10.1021/jo8013325
   PubMed Web of Science ®Google Scholar
• Procopio A , Cravotto G , Oliverio M , Costanzo P , Nardic M , Paonessa R . An eco-sustainable erbium(III)-catalyzed method for formation/cleavage of O-tert-butoxy carbonates . Green Chem . 2011 ; 13 : 436 – 443 . doi: 10.1039/c0gc00728e
   Google Scholar
• Matlack AS . Introduction to green chemistry . New York (NY) : Marcel Dekker Inc .: 2001 .
   Google Scholar
• Lancester M . Green chemistry: an introductory text . Cambridge : Royal Society of Chemistry ; 2002 .
   Google Scholar
• Clark JH , Macquarrie D . Handbook of green chemistry & technology . Oxford : Blackwell Publishers ; 2002 .
   Google Scholar
• Griero PA . Organic synthesis in water . London : Blakie ; 1998 .
   Google Scholar
• Tundo P , Annastas P , Black DS , Breen J , Collins T , Menoli S , Miyamoto J , Polyakoff M , Tumas W . Synthetic pathways and processes in green chemistry. Introductory overview . Pure Appl. Chem . 2000 ; 72 : 1207 – 1211 . doi: 10.1351/pac200072071207
   Web of Science ®Google Scholar
• Klai N , Berredjem M , Khettache N , Belghit M-Y , Regainia Z , Aouf N . Simple and efficient cleavage reaction of the boc group in heterocyclic compounds . J. Heterocycl. Chem . 2004 ; 41 : 57 – 60 . doi: 10.1002/jhet.5570410109
   Google Scholar
• Cheraiet Z , Ouarna S , Jamel Z , Berredjem M , Aouf N . A Simple and Efficient Green Method for the Deprotection of N-Boc in Various Structurally Diverse Amines under Water-mediated Catalyst-free Conditions . Int. J. of Chem . 2012 ; 4 : 73 – 79
   Google Scholar
• Cheraiet Z , Ouarna S , Hessainia S , Berredjem M , Aouf N . N-tert-Butoxycarbonylation of structurally diverse aminesand sulfamides under water-mediated catalyst-free conditions . ISRN org. chem . 2012 ; ID 404235 : 8 doi: 10.5402/2012/404235
   Google Scholar
• Alfonsi K , Colberg J , Dunn PJ , Fevig T , Jenings S , Johnson TA , Kleine HP , Knight C , Nagy MA , Perry DA , Stefaniak M . Green chemistry oriented organic synthesis in water . Green Chem . 2008 ; 10 : 31 – 36 . doi: 10.1039/b711717e
   Web of Science ®Google Scholar
• Wang J , Liang Y-L , Qu J . Boiling water-catalyzed neutral and selective N-Boc deprotection . Chem. Commun . 2009 ; 5144 – 5146 . doi: 10.1039/b910239f
   PubMedGoogle Scholar