Pd-Catalyzed cascade cyclization of: O -alkynylanilines via C-H/C-N bond cleavage leading to dibenzo [a, c] carbazoles

Sheng Zhang; Hengmin Ma; Hon Eong Ho; Yoshinori Yamamoto; Ming Bao; Tienan Jin

doi:10.1039/c8ob01386a

Pd-Catalyzed cascade cyclization of: O -alkynylanilines via C-H/C-N bond cleavage leading to dibenzo [a, c] carbazoles

Sheng Zhang, Hengmin Ma, Hon Eong Ho, Yoshinori Yamamoto, Ming Bao, Tienan Jin

SCI - Research and Analytical Center for Giant Molecules

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

4 Citations (Scopus)

Abstract

A new and efficient Pd-catalyzed cascade cyclization of biaryl-tethered o-alkynylanilines for the formation of dibenzo[a,c]carbazole derivatives has been reported. The use of the alkyl-substituted tertiary anilines together with the combination of the PdCl₂ catalyst with the MnO₂ oxidant and PivOH is vital for giving rise to 5-endo cyclization, C-N bond cleavage, and C-H bond activation in a cascade manner to produce the corresponding products with structural diversity.

Original language	English
Pages (from-to)	5236-5240
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	16
Issue number	29
DOIs	https://doi.org/10.1039/c8ob01386a
Publication status	Published - 2018 Jan 1

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Pd-Catalyzed cascade cyclization of: O -alkynylanilines via C-H/C-N bond cleavage leading to dibenzo [a, c] carbazoles",

abstract = "A new and efficient Pd-catalyzed cascade cyclization of biaryl-tethered o-alkynylanilines for the formation of dibenzo[a,c]carbazole derivatives has been reported. The use of the alkyl-substituted tertiary anilines together with the combination of the PdCl2 catalyst with the MnO2 oxidant and PivOH is vital for giving rise to 5-endo cyclization, C-N bond cleavage, and C-H bond activation in a cascade manner to produce the corresponding products with structural diversity.",

author = "Sheng Zhang and Hengmin Ma and Ho, {Hon Eong} and Yoshinori Yamamoto and Ming Bao and Tienan Jin",

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T2 - O -alkynylanilines via C-H/C-N bond cleavage leading to dibenzo [a, c] carbazoles

AU - Zhang, Sheng

AU - Ma, Hengmin

AU - Ho, Hon Eong

AU - Yamamoto, Yoshinori

AU - Bao, Ming

AU - Jin, Tienan

PY - 2018/1/1

Y1 - 2018/1/1

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AB - A new and efficient Pd-catalyzed cascade cyclization of biaryl-tethered o-alkynylanilines for the formation of dibenzo[a,c]carbazole derivatives has been reported. The use of the alkyl-substituted tertiary anilines together with the combination of the PdCl2 catalyst with the MnO2 oxidant and PivOH is vital for giving rise to 5-endo cyclization, C-N bond cleavage, and C-H bond activation in a cascade manner to produce the corresponding products with structural diversity.

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