Jump to main content
Jump to site search

Issue 1, 2016
Previous Article Next Article

Advanced 1,1-carboboration reactions with pentafluorophenylboranes

Author affiliations

Abstract

The 1,1 carboboration reaction of a variety of metal-substituted alkynes with simple trialkylboranes R3B yields the respective alkenylboranes (Wrackmeyer reaction). The use of the strongly electrophilic R-B(C6F5)2 reagents allows for much milder reaction conditions and gives good yields of the respective bulky alkenylboranes from conventional terminal alkynes by means of 1,2-hydride migration. Even internal alkynes undergo 1,1-carboboration with the R-B(C6F5)2 reagents, in this case yielding alkenylboranes by means of C–C bond cleavage. Phosphorus, sulfur or even boron containing substituents can serve as the migrating alkynyl substituents in the advanced 1,1-carboboration reactions using the R-B(C6F5)2 reagents. Sequential 1,1-carboboration of geminal bis(alkynyl) derivatives of these elements with the R-B(C6F5)2 boranes yields boryl substituted phospholes, thiophenes or even boroles in quite a variety. Vicinal bis(alkynyl)arenes or heteroarene substrates undergo benzannulation reactions in this way. Many of the -B(C6F5)2 substituted 1,1-carboboration products can be used as reagents in cross coupling reactions. A recently disclosed organometallic analogue, namely a 1,1-carbozirconation reaction is described.

Graphical abstract: Advanced 1,1-carboboration reactions with pentafluorophenylboranes

Back to tab navigation

Article information


Submitted
01 Sep 2015
Accepted
07 Oct 2015
First published
08 Oct 2015

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2016,7, 56-65
Article type
Perspective

Advanced 1,1-carboboration reactions with pentafluorophenylboranes

G. Kehr and G. Erker, Chem. Sci., 2016, 7, 56
DOI: 10.1039/C5SC03282B

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material.

Reproduced material should be attributed as follows:

  • For reproduction of material from NJC:
    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
  • For reproduction of material from PCCP:
    [Original citation] - Published by the PCCP Owner Societies.
  • For reproduction of material from PPS:
    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
  • For reproduction of material from all other RSC journals:
    [Original citation] - Published by The Royal Society of Chemistry.

Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.


Social activity

Search articles by author

Spotlight

Advertisements