An Annulative Synthetic Strategy for Building Triphenylene Frameworks by Multiple C-H Bond Activations.

Angew Chem Int Ed Engl 2017 04 30;56(18):5007-5011. Epub 2017 Mar 30.

School of Energy and Chemical Engineering, Ulsan National Institute of Science and Technology (UNIST), 50 UNIST-gil, Ulsan, 44919, Republic of Korea.

C-H activation is a versatile tool for appending aryl groups to aromatic systems. However, heavy demands on multiple catalytic cycle operations and site-selectivity have limited its use for graphene segment synthesis. A Pd-catal- yzed one-step synthesis of functionalized triphenylene frameworks is disclosed, which proceeds by 2- or 4-fold C-H arylation of unactivated benzene derivatives. A Pd (dibenzylideneacetone) catalytic system, using cyclic diaryliodonium salts as π-extending agents, leads to site-selective inter- and intramolecular tandem arylation sequences. Moreover, N-substituted triphenylenes are applied to a field-effect transistor sensor for rapid, sensitive, and reversible alcohol vapor detection.

Download full-text PDF

Source
http://dx.doi.org/10.1002/anie.201700405DOI Listing
April 2017
22 Reads

Publication Analysis

Top Keywords

triphenylene frameworks
8
sequences n-substituted
4
pd-catal- yzed
4
yzed one-step
4
synthesis pd-catal-
4
one-step synthesis
4
frameworks disclosed
4
arylation sequences
4
functionalized triphenylene
4
synthesis functionalized
4
n-substituted triphenylenes
4
segment synthesis
4
applied field-effect
4
cycle operations
4
catalytic cycle
4
π-extending agents
4
site-selectivity limited
4
graphene segment
4
limited graphene
4
triphenylenes applied
4

References

(Supplied by CrossRef)

Segawa et al.
Nat. Rev. Mater. 2016

Hirsch et al.
Nat. Mater. 2010

Geim et al.
Nat. Mater. 2007

Novoselov et al.
Science 2004

Narita et al.
Chem. Soc. Rev. 2015

Chen et al.
Angew. Chem. Int. Ed. 2012

Angew. Chem. 2012

Ozaki et al.
Nat. Commun. 2015

Kawasumi et al.
Nat. Chem. 2013

Dumslaff et al.
J. Am. Chem. Soc. 2016

Treier et al.
Nat. Chem. 2011

Similar Publications