Literature DB >> 21043508

Electrophilic aromatic substitution of a BN indole.

Eric R Abbey1, Lev N Zakharov, Shih-Yuan Liu.   

Abstract

We report the first examples of a "BN-fused" indole, and we demonstrate that this new family of unnatural indole derivatives undergoes electrophilic aromatic substitution (EAS) reactions with the same regioselectivity as its organic analogue. Competition experiments reveal that N-t-Bu-BN-indole is more nucleophilic in EAS reactions than its carbonaceous counterpart. X-ray structural analysis between BN indole and classic indole highlights significant differences in bond distances, in particular for bonds associated with the boron atom.

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Year:  2010        PMID： 21043508      PMCID： PMC2990470          DOI： 10.1021/ja107312u

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  19 in total

1.  Synthesis and functionalization of indoles through palladium-catalyzed reactions.

Authors:  Sandro Cacchi; Giancarlo Fabrizi
Journal:  Chem Rev       Date:  2005-07       Impact factor: 60.622

Review 2.  Chemistry and biology of monoterpene indole alkaloid biosynthesis.

Authors:  Sarah E O'Connor; Justin J Maresh
Journal:  Nat Prod Rep       Date:  2006-05-26       Impact factor: 13.423

Review 3.  Practical methodologies for the synthesis of indoles.

Authors:  Guy R Humphrey; Jeffrey T Kuethe
Journal:  Chem Rev       Date:  2006-07       Impact factor: 60.622

4.  A hybrid organic/inorganic benzene.

Authors:  Adam J V Marwitz; Myrna H Matus; Lev N Zakharov; David A Dixon; Shih-Yuan Liu
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

5.  Molecular double-bond covalent radii for elements Li-E112.

Authors:  Pekka Pyykkö; Michiko Atsumi
Journal:  Chemistry       Date:  2009-11-23       Impact factor: 5.236

6.  A general method for acylation of indoles at the 3-position with acyl chlorides in the presence of dialkylaluminum chloride.

Authors:  T Okauchi; M Itonaga; T Minami; T Owa; K Kitoh; H Yoshino
Journal:  Org Lett       Date:  2000-05-18       Impact factor: 6.005

7.  Crystal clear structural evidence for electron delocalization in 1,2-dihydro-1,2-azaborines.

Authors:  Eric R Abbey; Lev N Zakharov; Shih-Yuan Liu
Journal:  J Am Chem Soc       Date:  2008-05-14       Impact factor: 15.419

8.  Diversity through isosterism: the case of boron-substituted 1,2-dihydro-1,2-azaborines.

Authors:  Adam J V Marwitz; Eric R Abbey; Jesse T Jenkins; Lev N Zakharov; Shih-Yuan Liu
Journal:  Org Lett       Date:  2007-10-18       Impact factor: 6.005

9.  Boron mimetics: 1,2-dihydro-1,2-azaborines bind inside a nonpolar cavity of T4 lysozyme.

Authors:  Lijun Liu; Adam J V Marwitz; Brian W Matthews; Shih-Yuan Liu
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

10.  Elemental isomerism: a boron-nitrogen surrogate for a carbon-carbon double bond increases the chemical diversity of estrogen receptor ligands.

Authors:  Hai-Bing Zhou; Kendall W Nettles; John B Bruning; Younchang Kim; Andrzej Joachimiak; Sanjay Sharma; Kathryn E Carlson; Fabio Stossi; Benita S Katzenellenbogen; Geoffrey L Greene; John A Katzenellenbogen
Journal:  Chem Biol       Date:  2007-06
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  12 in total

Review 1.  Recent advances in azaborine chemistry.

Authors:  Patrick G Campbell; Adam J V Marwitz; Shih-Yuan Liu
Journal:  Angew Chem Int Ed Engl       Date:  2012-05-29       Impact factor: 15.336

2.  Boron in disguise: the parent "fused" BN indole.

Authors:  Eric R Abbey; Lev N Zakharov; Shih-Yuan Liu
Journal:  J Am Chem Soc       Date:  2011-07-13       Impact factor: 15.419

3.  Nucleophilic aromatic substitution reactions of 1,2-dihydro-1,2-azaborine.

Authors:  Ashley N Lamm; Edward B Garner; David A Dixon; Shih-Yuan Liu
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-12       Impact factor: 15.336

4.  Rhodium-catalyzed boron arylation of 1,2-azaborines.

Authors:  Gabriel E Rudebusch; Lev N Zakharov; Shih-Yuan Liu
Journal:  Angew Chem Int Ed Engl       Date:  2013-07-05       Impact factor: 15.336

5.  Cation-π binding ability of BN indole.

Authors:  Katherine Boknevitz; Clovis Darrigan; Anna Chrostowska; Shih-Yuan Liu
Journal:  Chem Commun (Camb)       Date:  2020-03-31       Impact factor: 6.222

6.  A 1,3-dihydro-1,3-azaborine debuts.

Authors:  Senmiao Xu; Lev N Zakharov; Shih-Yuan Liu
Journal:  J Am Chem Soc       Date:  2011-11-21       Impact factor: 15.419

Review 7.  BN isosteres of indole.

Authors:  Eric R Abbey; Shih-Yuan Liu
Journal:  Org Biomol Chem       Date:  2013-04-07       Impact factor: 3.876

8.  Protecting group-free synthesis of 1,2-azaborines: a simple approach to the construction of BN-benzenoids.

Authors:  Eric R Abbey; Ashley N Lamm; Andrew W Baggett; Lev N Zakharov; Shih-Yuan Liu
Journal:  J Am Chem Soc       Date:  2013-08-19       Impact factor: 15.419

9.  Selectivity in the Elaboration of Bicyclic Borazarenes.

Authors:  Ayan Bhattacharjee; Geraint H M Davies; Borna Saeednia; Steven R Wisniewski; Gary A Molander
Journal:  Adv Synth Catal       Date:  2020-12-23       Impact factor: 5.837

10.  Rhodium-catalyzed B-H activation of 1,2-azaborines: synthesis and characterization of BN isosteres of stilbenes.

Authors:  Alec N Brown; Lev N Zakharov; Tanya Mikulas; David A Dixon; Shih-Yuan Liu
Journal:  Org Lett       Date:  2014-06-11       Impact factor: 6.005
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