Investigation into the Organobismuth Dismutation and Its Use for Rational Synthesis of Heteroleptic Triarylbismuthanes, Ar1 2Ar2Bi

Organobismuthanes undergo dismutation, a substituent scrambling process, complicating the synthesis of unsymmetrically trisubstituted bismuthanes of the general formula Ar1 2Ar2Bi. Although the dismutation is a mechanistically diverse phenomenon, at ambient or lower temperatures, dismutation is trig...

Full description

Saved in:
Bibliographic Details
Published inOrganometallics Vol. 39; no. 6; pp. 778 - 782
Main Authors Louis-Goff, Thomas, Rheingold, Arnold L, Hyvl, Jakub
Format Journal Article
LanguageEnglish
Published American Chemical Society 23.03.2020
Online AccessGet full text

Cover

More Information
Summary:Organobismuthanes undergo dismutation, a substituent scrambling process, complicating the synthesis of unsymmetrically trisubstituted bismuthanes of the general formula Ar1 2Ar2Bi. Although the dismutation is a mechanistically diverse phenomenon, at ambient or lower temperatures, dismutation is triggered mainly by an electrophilic bismuth source. Therefore, the selection of the electrophile, Ar1 2BiX (X = tosylate or iodide if Ar1 = mesityl) or Ar1BiX2 (X = tosylate), and its use in low concentration during the reaction is key to suppressing the dismutation, leading to new, streamlined protocols utilizing direct arylations of Ar1 2BiX (X = OTs or I) or Ar1Bi­(OTs)2 with organozincs affording heteroleptic triarylbismuthanes Ar1 2Ar2Bi.
ISSN:0276-7333
1520-6041
DOI:10.1021/acs.organomet.9b00777