Palladium/Silver-Cocatalyzed Tandem Reactions of Oxabenzonorbornadienes with Substituted Arylacetylenes: A Simple Method for the Preparation of 1,2-Diarylethanones and 1,2-Diarylacetylenes

Jingchao Chen; Shanshan Liu; Yongyun Zhou; Sifeng Li; Chengyuan Lin; Zhaoxiang Bian; Baomin Fan

doi:10.1021/acs.organomet.5b00551

Palladium/Silver-Cocatalyzed Tandem Reactions of Oxabenzonorbornadienes with Substituted Arylacetylenes: A Simple Method for the Preparation of 1,2-Diarylethanones and 1,2-Diarylacetylenes

Jingchao Chen, Shanshan Liu, Yongyun Zhou, Sifeng Li, Chengyuan Lin, Zhaoxiang Bian, Baomin Fan^*

^*Corresponding author for this work

Research output: Contribution to journal › Journal article › peer-review

26 Citations (Scopus)

Abstract

The effective synthesis of 1,2-diarylethanones was achieved using palladium(II) acetate [Pd(OAc)₂] and silver triflate (AgOTf) as cocatalysts from various oxabenzonorbornadiene derivatives and substituted arylacetylenes via tandem reactions under mild conditions. Exploration of the oxabenzonorbornadiene substrates showed that the 1,2-diarylacetylenes were obtained from adjacent alkoxy substituted oxabenzonorbornadiene derivatives. Preliminary mechanistic studies indicate that the AgOTf served as an indispensable catalyst, and the mechanism of the tandem reaction was proposed.

Original language	English
Pages (from-to)	4318-4322
Number of pages	5
Journal	Organometallics
Volume	34
Issue number	17
DOIs	https://doi.org/10.1021/acs.organomet.5b00551
Publication status	Published - 14 Sept 2015

Scopus Subject Areas

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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title = "Palladium/Silver-Cocatalyzed Tandem Reactions of Oxabenzonorbornadienes with Substituted Arylacetylenes: A Simple Method for the Preparation of 1,2-Diarylethanones and 1,2-Diarylacetylenes",

abstract = "The effective synthesis of 1,2-diarylethanones was achieved using palladium(II) acetate [Pd(OAc)2] and silver triflate (AgOTf) as cocatalysts from various oxabenzonorbornadiene derivatives and substituted arylacetylenes via tandem reactions under mild conditions. Exploration of the oxabenzonorbornadiene substrates showed that the 1,2-diarylacetylenes were obtained from adjacent alkoxy substituted oxabenzonorbornadiene derivatives. Preliminary mechanistic studies indicate that the AgOTf served as an indispensable catalyst, and the mechanism of the tandem reaction was proposed.",

author = "Jingchao Chen and Shanshan Liu and Yongyun Zhou and Sifeng Li and Chengyuan Lin and Zhaoxiang Bian and Baomin Fan",

note = "Funding information: We thank the National Natural Science Foundation of China (21362043, 21162040, 21302162), the Government of Yunnan Province (2012FB170), and the State Key Laboratory of Elemento-organic Chemistry, Nankai University (201302), for financial support. Publisher copyright: {\textcopyright} 2015 American Chemical Society",

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doi = "10.1021/acs.organomet.5b00551",

language = "English",

volume = "34",

pages = "4318--4322",

journal = "Organometallics",

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Palladium/Silver-Cocatalyzed Tandem Reactions of Oxabenzonorbornadienes with Substituted Arylacetylenes: A Simple Method for the Preparation of 1,2-Diarylethanones and 1,2-Diarylacetylenes. / Chen, Jingchao; Liu, Shanshan; Zhou, Yongyun et al.
In: Organometallics, Vol. 34, No. 17, 14.09.2015, p. 4318-4322.

Research output: Contribution to journal › Journal article › peer-review

TY - JOUR

T1 - Palladium/Silver-Cocatalyzed Tandem Reactions of Oxabenzonorbornadienes with Substituted Arylacetylenes

T2 - A Simple Method for the Preparation of 1,2-Diarylethanones and 1,2-Diarylacetylenes

AU - Chen, Jingchao

AU - Liu, Shanshan

AU - Zhou, Yongyun

AU - Li, Sifeng

AU - Lin, Chengyuan

AU - Bian, Zhaoxiang

AU - Fan, Baomin

N1 - Funding information: We thank the National Natural Science Foundation of China (21362043, 21162040, 21302162), the Government of Yunnan Province (2012FB170), and the State Key Laboratory of Elemento-organic Chemistry, Nankai University (201302), for financial support. Publisher copyright: © 2015 American Chemical Society

PY - 2015/9/14

Y1 - 2015/9/14

N2 - The effective synthesis of 1,2-diarylethanones was achieved using palladium(II) acetate [Pd(OAc)2] and silver triflate (AgOTf) as cocatalysts from various oxabenzonorbornadiene derivatives and substituted arylacetylenes via tandem reactions under mild conditions. Exploration of the oxabenzonorbornadiene substrates showed that the 1,2-diarylacetylenes were obtained from adjacent alkoxy substituted oxabenzonorbornadiene derivatives. Preliminary mechanistic studies indicate that the AgOTf served as an indispensable catalyst, and the mechanism of the tandem reaction was proposed.

AB - The effective synthesis of 1,2-diarylethanones was achieved using palladium(II) acetate [Pd(OAc)2] and silver triflate (AgOTf) as cocatalysts from various oxabenzonorbornadiene derivatives and substituted arylacetylenes via tandem reactions under mild conditions. Exploration of the oxabenzonorbornadiene substrates showed that the 1,2-diarylacetylenes were obtained from adjacent alkoxy substituted oxabenzonorbornadiene derivatives. Preliminary mechanistic studies indicate that the AgOTf served as an indispensable catalyst, and the mechanism of the tandem reaction was proposed.

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U2 - 10.1021/acs.organomet.5b00551

DO - 10.1021/acs.organomet.5b00551

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JO - Organometallics

JF - Organometallics

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Palladium/Silver-Cocatalyzed Tandem Reactions of Oxabenzonorbornadienes with Substituted Arylacetylenes: A Simple Method for the Preparation of 1,2-Diarylethanones and 1,2-Diarylacetylenes

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