Copper-Catalyzed Direct Transformation of Secondary Allylic and Benzylic Alcohols into Azides and Amides: An Efficient Utility of Azide as a Nitrogen Source

被引:17
作者
Rokade, Balaji V. [1 ]
Gadde, Karthik [1 ]
Prabhu, Kandikere Ramaiah [1 ]
机构
[1] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India
关键词
Synthetic methods; Chemoselectivity; Alcohols; Azides; Amides; Copper; C-H; DIRECT CONVERSION; OXIDATIVE TRANSFORMATION; COUPLING REACTIONS; CLICK CHEMISTRY; ORGANIC AZIDES; PRIMARY AMINES; BOND FORMATION; ALKYL AZIDES; AZIDATION;
D O I
10.1002/ejoc.201500010
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A mild and convenient method for the synthesis of amides has been explored by using secondary alcohols, Cu(ClO4)(2)6H(2)O as a catalyst, and trimethylsilyl azide (TMSN3) as a nitrogen source in the presence of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) at ambient temperature. This method has been successfully adapted to the preparation of azides directly from their corresponding alcohols and offers excellent chemoselectivity in the formation of -halo azides and the azidation of allylic alcohols in the presence of a benzyl alcohol moiety. In addition, this strategy provides an opportunity to synthesize azides that can serve as precursors to -amino acids.
引用
收藏
页码:2706 / 2717
页数:12
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共 114 条
[61]   Cinnamoyl inhibitors of tissue transglutaminase [J].
Pardin, Christophe ;
Pelletier, Joelle N. ;
Lubell, William D. ;
Keillor, Jeffrey W. .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (15) :5766-5775
[62]   Chemoselective three-component synthesis of homoallylic azides using an FeCl3 catalyst [J].
Pramanik, Suman ;
Ghorai, Prasanta .
RSC ADVANCES, 2013, 3 (45) :23157-23165
[63]   2-Pyridylsulfinamides as effective catalysts in the asymmetric alkylation of aldehydes with diethylzinc [J].
Prasad, Kavirayani R. ;
Revu, Omkar .
TETRAHEDRON, 2013, 69 (39) :8422-8428
[64]   Looking for a Paradigm for the Reactivity of Phenonium Ions [J].
Protti, Stefano ;
Dondi, Daniele ;
Mella, Mariella ;
Fagnoni, Maurizio ;
Albini, Angelo .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (17) :3229-3237
[65]   Selective Csp2-Csp Bond Cleavage: The Nitrogenation of Alkynes to Amides [J].
Qin, Chong ;
Feng, Peng ;
Ou, Yang ;
Shen, Tao ;
Wang, Teng ;
Jiao, Ning .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (30) :7850-7854
[66]   Iron-Catalyzed C?H and C?C Bond Cleavage: A Direct Approach to Amides from Simple Hydrocarbons [J].
Qin, Chong ;
Zhou, Wang ;
Chen, Feng ;
Ou, Yang ;
Jiao, Ning .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (52) :12595-12599
[67]   Iron-Facilitated Direct Oxidative C-H Transformation of Allylarenes or Alkenes to Alkenyl Nitriles [J].
Qin, Chong ;
Jiao, Ning .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (45) :15893-15895
[68]   Direct transformation of arylpropynes to acrylamides via a three-step tandem reaction [J].
Qiu, Jun ;
Zhang, Ronghua .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (10) :1556-1560
[69]   DDQ-promoted direct transformation of benzyl hydrocarbons to amides via tandem reaction of the CDC reaction and Beckmann rearrangement [J].
Qiu, Jun ;
Zhang, Ronghua .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (36) :6008-6012
[70]   A Palladium-Catalyzed Carbonylation Approach to Acid Chloride Synthesis [J].
Quesnel, Jeffrey S. ;
Arndtsen, Bruce A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (45) :16841-16844