Synthesis of triaryltriazasumanenes

Patcharin Kaewmati; Qitao Tan; Shuhei Higashibayashi; Yumi Yakiyama; Hidehiro Sakurai

doi:10.1246/cl.160978

Synthesis of triaryltriazasumanenes

Patcharin Kaewmati, Qitao Tan, Shuhei Higashibayashi, Yumi Yakiyama, Hidehiro Sakurai

Research output: Contribution to journal › Article › peer-review

27 Citations (Scopus)

Abstract

C₃-symmetric chiral triaryltriazasumanenes were successfully prepared in good yields by Pd-catalyzed cross-coupling reactions of chiral tris(methylthio)triazasumanene with various arylboronic acids. These chiral triaryltriazasumanenes showed very stable bowl chirality without racemization at room temperature. Single-crystal X-ray crystallography of the p-(trifluoromethyl)phenyl derivative revealed the formation of unidirectional π-π stacking columns that were connected by F⋯F interactions unlike the noncolumnar crystal packing of tris(methanesulfonyl)triazasumanene.

Original language	English
Pages (from-to)	146-148
Number of pages	3
Journal	Chemistry Letters
Volume	46
Issue number	1
DOIs	https://doi.org/10.1246/cl.160978
Publication status	Published - 2017
Externally published	Yes

Keywords

Pd-catalyzed cross coupling
Triazasumanene
Unidirectional columnar packing

ASJC Scopus subject areas

Chemistry(all)

Access to Document

10.1246/cl.160978

Cite this

@article{6b51c2c9351c41ef85846b9a9ae774cc,

title = "Synthesis of triaryltriazasumanenes",

abstract = "C3-symmetric chiral triaryltriazasumanenes were successfully prepared in good yields by Pd-catalyzed cross-coupling reactions of chiral tris(methylthio)triazasumanene with various arylboronic acids. These chiral triaryltriazasumanenes showed very stable bowl chirality without racemization at room temperature. Single-crystal X-ray crystallography of the p-(trifluoromethyl)phenyl derivative revealed the formation of unidirectional π-π stacking columns that were connected by F⋯F interactions unlike the noncolumnar crystal packing of tris(methanesulfonyl)triazasumanene.",

keywords = "Pd-catalyzed cross coupling, Triazasumanene, Unidirectional columnar packing",

author = "Patcharin Kaewmati and Qitao Tan and Shuhei Higashibayashi and Yumi Yakiyama and Hidehiro Sakurai",

note = "Funding Information: This work was supported by a Grant-in-Aid for Scientific Research on Innovative Area {"}π Space Figuration{"} from MEXT (No. 26102002), and JSPS KAKENHI (No. 26288020). Q. T acknowledges JSPS for the scholarship. S.H. acknowledges ACT-C, JST for the support. Publisher Copyright: {\textcopyright} 2017 The Chemical Society of Japan.",

year = "2017",

doi = "10.1246/cl.160978",

language = "English",

volume = "46",

pages = "146--148",

journal = "Chemistry Letters",

issn = "0366-7022",

publisher = "Chemical Society of Japan",

number = "1",

}

TY - JOUR

T1 - Synthesis of triaryltriazasumanenes

AU - Kaewmati, Patcharin

AU - Tan, Qitao

AU - Higashibayashi, Shuhei

AU - Yakiyama, Yumi

AU - Sakurai, Hidehiro

N1 - Funding Information: This work was supported by a Grant-in-Aid for Scientific Research on Innovative Area "π Space Figuration" from MEXT (No. 26102002), and JSPS KAKENHI (No. 26288020). Q. T acknowledges JSPS for the scholarship. S.H. acknowledges ACT-C, JST for the support. Publisher Copyright: © 2017 The Chemical Society of Japan.

PY - 2017

Y1 - 2017

N2 - C3-symmetric chiral triaryltriazasumanenes were successfully prepared in good yields by Pd-catalyzed cross-coupling reactions of chiral tris(methylthio)triazasumanene with various arylboronic acids. These chiral triaryltriazasumanenes showed very stable bowl chirality without racemization at room temperature. Single-crystal X-ray crystallography of the p-(trifluoromethyl)phenyl derivative revealed the formation of unidirectional π-π stacking columns that were connected by F⋯F interactions unlike the noncolumnar crystal packing of tris(methanesulfonyl)triazasumanene.

AB - C3-symmetric chiral triaryltriazasumanenes were successfully prepared in good yields by Pd-catalyzed cross-coupling reactions of chiral tris(methylthio)triazasumanene with various arylboronic acids. These chiral triaryltriazasumanenes showed very stable bowl chirality without racemization at room temperature. Single-crystal X-ray crystallography of the p-(trifluoromethyl)phenyl derivative revealed the formation of unidirectional π-π stacking columns that were connected by F⋯F interactions unlike the noncolumnar crystal packing of tris(methanesulfonyl)triazasumanene.

KW - Pd-catalyzed cross coupling

KW - Triazasumanene

KW - Unidirectional columnar packing

UR - http://www.scopus.com/inward/record.url?scp=85011554700&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85011554700&partnerID=8YFLogxK

U2 - 10.1246/cl.160978

DO - 10.1246/cl.160978

M3 - Article

AN - SCOPUS:85011554700

SN - 0366-7022

VL - 46

SP - 146

EP - 148

JO - Chemistry Letters

JF - Chemistry Letters

IS - 1

ER -

Synthesis of triaryltriazasumanenes

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this