Novel Route to Enantiopure 2,2'-Diaryl-1,1'-binaphthalenes by Stereoconservative Suzuki Arylation at Positions 2 and 2'

[img]PDF - Authorized users only
Language: English
239Kb
Title:Novel Route to Enantiopure 2,2'-Diaryl-1,1'-binaphthalenes by Stereoconservative Suzuki Arylation at Positions 2 and 2'
Creators:
Brath, Henrich
Dubovská, Margaréta
Juríček, Michal
Kasák, Peter
Putala, Martin
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 69, 7, pp. 1517-1536
Uncontrolled Keywords:C-C coupling, Binapthyls, Palladium, Boronic acids, Biaryls, Stereoselective synthesis, Steric hindrance, <i>C</i><sub>2</sub>-Symmetry, Cross-coupling reactions

Abstract

The Suzuki arylation of enantiopure 2,2'-diiodo-1,1'-binaphthalene affords the 2,2'-diarylated products in considerable yields (up to 52%), however, significantly racemized. The reversed-polarity approach, using novel enantiopure 1,1'-binaphthalene-2,2'-diyldiboronic acid, prepared either by resolution or by stereoconservative boronation, allowed, after optimization of coupling conditions, to obtain the model 2,2'-ditolylated product in good yield (56%) as well, but in addition, without impairing of enantiomeric purity (i.e. stereoconservatively). The developed synthetic approach was found to be an expedient method for&nbsp;the synthesis of enantiopure 2,2'-diaryl-1,1'-binaphthalenes, especially for those with electron-neutral and electron-deficient poor aryl groups. Observing that the diboronic acid decomposes by hydrodeboronation under the reaction conditions, 2-aryl-1,1'-binaphthalenes&nbsp;were isolated as the main products from the reaction with less reactive electron-rich aryl iodides. <p>

Title:Novel Route to Enantiopure 2,2'-Diaryl-1,1'-binaphthalenes by Stereoconservative Suzuki Arylation at Positions 2 and 2'
Creators:
Brath, Henrich
Dubovská, Margaréta
Juríček, Michal
Kasák, Peter
Putala, Martin
Uncontrolled Keywords:C-C coupling, Binapthyls, Palladium, Boronic acids, Biaryls, Stereoselective synthesis, Steric hindrance, <i>C</i><sub>2</sub>-Symmetry, Cross-coupling reactions
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:69
Number:7
Page Range:pp. 1517-1536
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20041517UNSPECIFIED
ID Code:2291
Item Type:Article
Deposited On:06 Feb 2009 17:17
Last Modified:06 Feb 2009 16:17

Citation

Brath, Henrich; Dubovská, Margaréta; Juríček, Michal; Kasák, Peter; Putala, Martin (2004) Novel Route to Enantiopure 2,2'-Diaryl-1,1'-binaphthalenes by Stereoconservative Suzuki Arylation at Positions 2 and 2'. Collection of Czechoslovak Chemical Communications, 69 (7). pp. 1517-1536. ISSN 0010-0765

Repository Staff Only: item control page