Journal
CELL REPORTS PHYSICAL SCIENCE
Volume 1, Issue 2, Pages -Publisher
CELL PRESS
DOI: 10.1016/j.xcrp.2020.100016
Keywords
-
Categories
Funding
- EPSRC [EP/L016443/1, EP/L000202, EP/R029431, EP/R026912/1]
- Leverhulme Trust [RPG-2016-020]
- EPSRC [EP/R026912/1] Funding Source: UKRI
Ask authors/readers for more resources
Advances in the chemistry of metal-free systems known as frustrated Lewis pairs (FLPs) has exposed new reactivity of the p-block elements, particularly in small-molecule activation and catalysis. Typically, the mode of activation by FLPs has been predicated on a heterolytic two-electron process, although recently, select FLPs have been shown to participate in single-electron processes. Here, we report the reaction of diary! substituted esters with FLPs. This results in divergent pathways, one whereby the diaryl moiety is stabilized by the Lewis basic phosphine, and the alternative pathway, wherein a single-electron transfer process occurs, generating the [Mes(3)P](+-)/[C(H)Ar-2](-) radical ion pair. The latter species undergoes a homocoupling reaction to yield tetraphenylethane derivatives. In the presence of olefins, this reactivity can be harnessed through an sp(2)-sp(3) C-C heterocoupling reaction to generate alpha,beta-substituted olefins, Notably, this work showcases an FLP approach to metal-free radical C-H bond activation with subsequent C-C bond formation, which also displays complementary reactivity to other approaches.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available