Literature DB >> 17580888

C-C bond-forming reactions via Pd-mediated decarboxylative alpha-imino anion generation.

Andrew A Yeagley1, Jason J Chruma.   

Abstract

Alpha-imino anions are generated under neutral reaction conditions via a Pd-mediated decarboxylation of allyl diphenylglycinate imines with concomitant formation of a pi-allylpalladium species. The resulting delocalized anion can attack the pi-allyl-Pd(II) species or be intercepted by aldehydes to afford homoallylic amines or protected 1,2-amino alcohols, respectively.

Entities:  

Year:  2007        PMID： 17580888     DOI： 10.1021/ol071080f

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  13 in total

1.  Synthesis of diarylmethylamines via palladium-catalyzed regioselective arylation of 1,1,3-triaryl-2-azaallyl anions.

Authors:  Minyan Li; Baris Yücel; Javier Adrio; Ana Bellomo; Patrick J Walsh
Journal:  Chem Sci       Date:  2014-06-01       Impact factor: 9.825

2.  Deacylative allylation: allylic alkylation via retro-Claisen activation.

Authors:  Alexander J Grenning; Jon A Tunge
Journal:  J Am Chem Soc       Date:  2011-08-24       Impact factor: 15.419

Review 3.  Transition metal-catalyzed decarboxylative allylation and benzylation reactions.

Authors:  Jimmie D Weaver; Antonio Recio; Alexander J Grenning; Jon A Tunge
Journal:  Chem Rev       Date:  2011-01-14       Impact factor: 60.622

4.  Palladium-catalyzed C(sp(3))-H Arylation of N-Boc benzylalkylamines via a deprotonative cross-coupling process.

Authors:  Nusrah Hussain; Byeong-Seon Kim; Patrick J Walsh
Journal:  Chemistry       Date:  2015-06-30       Impact factor: 5.236

5.  Migratory decarboxylative coupling of coumarins: synthetic and mechanistic aspects.

Authors:  Ranjan Jana; James J Partridge; Jon A Tunge
Journal:  Angew Chem Int Ed Engl       Date:  2011-04-19       Impact factor: 15.336

6.  Rapid decarboxylative allylation of nitroalkanes.

Authors:  Alexander J Grenning; Jon A Tunge
Journal:  Org Lett       Date:  2010-02-19       Impact factor: 6.005

7.  Regiospecific decarboxylative allylation of nitriles.

Authors:  Antonio Recio; Jon A Tunge
Journal:  Org Lett       Date:  2009-12-17       Impact factor: 6.005

8.  Dual Catalytic Decarboxylative Allylations of α-Amino Acids and Their Divergent Mechanisms.

Authors:  Simon B Lang; Kathryn M O'Nele; Justin T Douglas; Jon A Tunge
Journal:  Chemistry       Date:  2015-11-03       Impact factor: 5.236

9.  Intercepted Decarboxylative Allylations of Nitroalkanoates.

Authors:  Meghan Schmitt; Alexander J Grenning; Jon A Tunge
Journal:  Tetrahedron Lett       Date:  2012-06-07       Impact factor: 2.415

10.  Ligand-controlled asymmetric arylation of aliphatic α-amino anion equivalents.

Authors:  Ye Zhu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2014-03-13       Impact factor: 15.419
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