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

12 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

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",

note = "Funding Information: We are grateful to the National Natural Science Foundation of China (No. 21372035, 21573032, and 21602026) and the China Postdoctoral Science Foundation (No. 2016M590226) for their financial support. TJ thanks the Japan Society for Promotion of Science (JSPS) KAKENHI grant number 15KK0180 on Fostering Joint International Research. Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2018.",

year = "2018",

doi = "10.1039/c8ob01386a",

language = "English",

volume = "16",

pages = "5236--5240",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "29",

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TY - JOUR

T1 - Pd-Catalyzed cascade cyclization of

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

N1 - Funding Information: We are grateful to the National Natural Science Foundation of China (No. 21372035, 21573032, and 21602026) and the China Postdoctoral Science Foundation (No. 2016M590226) for their financial support. TJ thanks the Japan Society for Promotion of Science (JSPS) KAKENHI grant number 15KK0180 on Fostering Joint International Research. Publisher Copyright: © The Royal Society of Chemistry 2018.

PY - 2018

Y1 - 2018

N2 - 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.

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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DO - 10.1039/c8ob01386a

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VL - 16

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EP - 5240

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

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IS - 29

ER -

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

Abstract

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