Selective Oxidation of Amines to Aldehydes or Imines using Laccase‐Mediated Bio‐Oxidation

Advanced Synthesis and Catalysis - Tập 357 Số 8 - Trang 1840-1848 - 2015
Paola Galletti1, Federica Funiciello1, Roberto Soldati1, Daria Giacomini1
1Department of Chemistry “G. Ciamician,” University of Bologna, 40126 Bologna, Italy

Tóm tắt

AbstractAn efficient and practical chemo‐enzymatic aerobic oxidation in water of benzylamines to obtain aldehydes or imines is described. Laccase from Trametes versicolor was chosen as biocatalyst, and TEMPO (radical 2,2,6,6‐tetramethylpiperidine 1‐oxyl) as mediator. A study on the pH dependence of the aqueous medium allowed us to realise a fine tuning on product selectivity. Under our optimized reaction conditions, the bio‐oxidation of a series of primary, secondary and cyclic amines has been achieved.magnified image

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Tài liệu tham khảo

Turcotte M. G., 2001, Amines, Lower Aliphatic Amines, in: Kirk‐Othmer Encyclopedia of Chemical Technology, 10.1002

 

10.1002/ejoc.201300315

10.1021/cr300527g

 

10.1021/cs300212q

10.1002/chem.200401082

10.1039/c0ob00043d

 

10.1039/c2ob06670j

10.1039/c2sc20699d

 

10.1039/C3CC47081D

10.1002/adsc.200404110

 

10.1002/cssc.201301340

10.1002/cctc.201000175

 

10.1007/s10562-011-0758-0

10.1039/b700555e

 

10.1039/c3gc41186a

10.1039/c1cc13202d

 

10.1039/c4cc01671h

10.1039/c3cc41407h

 

10.1002/cctc.201200042

10.1021/cr100334x

10.1021/cr200013n

 

10.1039/C0GC00595A

10.1002/9783527611522

 

10.1021/cr400327t

10.1021/cr200111v

10.1021/bi020246b

 

10.1021/ja411692v

10.1126/science.1232220

10.1002/ange.201200587

10.1002/anie.201200587

10.1021/ol301095j

 

10.1007/s00018-009-0169-1

10.1002/adsc.200800775

 

10.1016/j.tibtech.2013.04.002

10.1016/j.procbio.2012.05.006

10.1016/j.biotechadv.2010.05.002

 

10.1002/adsc.201300960

10.1002/poc.812

 

10.1016/j.tibtech.2006.03.006

10.1016/j.tet.2005.12.076

10.1002/cssc.201402136

 

10.1002/adsc.201400260

10.1039/C4GC00901K

10.1002/adsc.201300501

10.1042/BST20060304

10.1007/s00253-004-1860-7

For the dependence of Laccase Tv activity on pH see for instance:

10.4014/jmb.1401.01025

10.1016/j.chemosphere.2012.03.019

10.1021/ol203096f

 

10.1021/ja306934b

J. F.Dellaria W. H.Moser M. R.Radmer G. W.Griesgraber PCT Int. Appl.WO 2007028129 A1 2007.

10.1039/c2gc16681j

 

10.1039/b516719a

10.1002/1099-0690(200212)2002:24<4195::AID-EJOC4195>3.0.CO;2-X