Palladium/Copper Complexes Co-Catalyzed Highly Enantioselective Ring Opening Reaction of Azabenzonorbornadienes with Terminal Alkynes

Baomin Fan; Sifeng Li; Hualei Chen; Zhiwu Lu; Shanshan Liu; Qingjing Yang; Lu Yu; Jianbin Xu; Yongyun Zhou; Jun Wang

doi:10.1002/adsc.201300748

Palladium/Copper Complexes Co-Catalyzed Highly Enantioselective Ring Opening Reaction of Azabenzonorbornadienes with Terminal Alkynes

Baomin Fan^*
, Sifeng Li
, Hualei Chen
, Zhiwu Lu
, Shanshan Liu
, Qingjing Yang
, Lu Yu
, Jianbin Xu
, Yongyun Zhou
, Jun Wang^*

^*Corresponding author for this work

Department of Chemistry

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

39 Citations (Scopus)

Abstract

A chiral palladium/copper (Pd/Cu) co-catalytic system which could enable asymmetric ring opening reaction of azabenzonorbornadienes with terminal alkynes is reported. This system comprises palladium(II) acetate [Pd(OAc)₂]/(R)-xyl-Binap and copper(I) triflate (CuOTf). A good substrate scope was found, with excellent enantioselective outcomes (up to >99.9 % ee). A reaction mechanism involving two metal complexes is also proposed.

Original language	English
Pages (from-to)	2827-2832
Number of pages	6
Journal	Advanced Synthesis & Catalysis
Volume	355
Issue number	14-15
DOIs	https://doi.org/10.1002/adsc.201300748
Publication status	Published - 11 Oct 2013

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10.1002/adsc.201300748

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title = "Palladium/Copper Complexes Co-Catalyzed Highly Enantioselective Ring Opening Reaction of Azabenzonorbornadienes with Terminal Alkynes",

abstract = "A chiral palladium/copper (Pd/Cu) co-catalytic system which could enable asymmetric ring opening reaction of azabenzonorbornadienes with terminal alkynes is reported. This system comprises palladium(II) acetate [Pd(OAc)2]/(R)-xyl-Binap and copper(I) triflate (CuOTf). A good substrate scope was found, with excellent enantioselective outcomes (up to >99.9 \% ee). A reaction mechanism involving two metal complexes is also proposed.",

author = "Baomin Fan and Sifeng Li and Hualei Chen and Zhiwu Lu and Shanshan Liu and Qingjing Yang and Lu Yu and Jianbin Xu and Yongyun Zhou and Jun Wang",

year = "2013",

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day = "11",

doi = "10.1002/adsc.201300748",

language = "English",

volume = "355",

pages = "2827--2832",

journal = "Advanced Synthesis \& Catalysis",

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T1 - Palladium/Copper Complexes Co-Catalyzed Highly Enantioselective Ring Opening Reaction of Azabenzonorbornadienes with Terminal Alkynes

AU - Fan, Baomin

AU - Li, Sifeng

AU - Chen, Hualei

AU - Lu, Zhiwu

AU - Liu, Shanshan

AU - Yang, Qingjing

AU - Yu, Lu

AU - Xu, Jianbin

AU - Zhou, Yongyun

AU - Wang, Jun

PY - 2013/10/11

Y1 - 2013/10/11

N2 - A chiral palladium/copper (Pd/Cu) co-catalytic system which could enable asymmetric ring opening reaction of azabenzonorbornadienes with terminal alkynes is reported. This system comprises palladium(II) acetate [Pd(OAc)2]/(R)-xyl-Binap and copper(I) triflate (CuOTf). A good substrate scope was found, with excellent enantioselective outcomes (up to >99.9 % ee). A reaction mechanism involving two metal complexes is also proposed.

AB - A chiral palladium/copper (Pd/Cu) co-catalytic system which could enable asymmetric ring opening reaction of azabenzonorbornadienes with terminal alkynes is reported. This system comprises palladium(II) acetate [Pd(OAc)2]/(R)-xyl-Binap and copper(I) triflate (CuOTf). A good substrate scope was found, with excellent enantioselective outcomes (up to >99.9 % ee). A reaction mechanism involving two metal complexes is also proposed.

UR - http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=ORCID&SrcApp=OrcidOrg&DestLinkType=FullRecord&DestApp=WOS_CPL&KeyUT=WOS:000328149300015&KeyUID=WOS:000328149300015

U2 - 10.1002/adsc.201300748

DO - 10.1002/adsc.201300748

M3 - Journal article

SN - 1615-4150

VL - 355

SP - 2827

EP - 2832

JO - Advanced Synthesis & Catalysis

JF - Advanced Synthesis & Catalysis

IS - 14-15

ER -

Palladium/Copper Complexes Co-Catalyzed Highly Enantioselective Ring Opening Reaction of Azabenzonorbornadienes with Terminal Alkynes

Abstract

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