Nickel-Catalyzed Asymmetric Reductive Heck Cyclization of Aryl Halides to Afford Indolines
A nickel‐catalyzed asymmetric reductive Heck reaction of aryl chlorides has been developed that affords substituted indolines with high enantioselectivity. Manganese powder is used as the terminal reductant with water as a proton source. Mechanistically, it is distinct from the palladium‐catalyzed p...
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sg-ntu-dr.10356-890282023-02-28T19:34:28Z Nickel-Catalyzed Asymmetric Reductive Heck Cyclization of Aryl Halides to Afford Indolines Qin, Xurong Lee, Marcus Wen Yao Zhou, Steve Jianrong School of Physical and Mathematical Sciences Asymmetric Catalysis Cyclization A nickel‐catalyzed asymmetric reductive Heck reaction of aryl chlorides has been developed that affords substituted indolines with high enantioselectivity. Manganese powder is used as the terminal reductant with water as a proton source. Mechanistically, it is distinct from the palladium‐catalyzed process in that the nickel–carbon bond is converted into a C−H bond to release the product through protonation instead of hydride donation followed by C−H reductive elimination on Pd. MOE (Min. of Education, S’pore) Accepted version 2018-06-01T03:49:09Z 2019-12-06T17:16:15Z 2018-06-01T03:49:09Z 2019-12-06T17:16:15Z 2017 2017 Journal Article Qin, X., Lee, M. W. Y., & Zhou, S. J. (2017). Nickel‐Catalyzed Asymmetric Reductive Heck Cyclization of Aryl Halides to Afford Indolines. Angewandte Chemie International Edition, 56(41), 12723-12726. 1433-7851 https://hdl.handle.net/10356/89028 http://hdl.handle.net/10220/44927 10.1002/anie.201707134 207470 en Angewandte Chemie International Edition © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. This is the author created version of a work that has been peer reviewed and accepted for publication by Angewandte Chemie International Edition, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. It incorporates referee’s comments but changes resulting from the publishing process, such as copyediting, structural formatting, may not be reflected in this document. The published version is available at: [http://dx.doi.org/10.1002/anie.201707134]. 5 p. application/pdf |
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Asymmetric Catalysis Cyclization |
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Asymmetric Catalysis Cyclization Qin, Xurong Lee, Marcus Wen Yao Zhou, Steve Jianrong Nickel-Catalyzed Asymmetric Reductive Heck Cyclization of Aryl Halides to Afford Indolines |
| description |
A nickel‐catalyzed asymmetric reductive Heck reaction of aryl chlorides has been developed that affords substituted indolines with high enantioselectivity. Manganese powder is used as the terminal reductant with water as a proton source. Mechanistically, it is distinct from the palladium‐catalyzed process in that the nickel–carbon bond is converted into a C−H bond to release the product through protonation instead of hydride donation followed by C−H reductive elimination on Pd. |
| author2 |
School of Physical and Mathematical Sciences |
| author_facet |
School of Physical and Mathematical Sciences Qin, Xurong Lee, Marcus Wen Yao Zhou, Steve Jianrong |
| format |
Article |
| author |
Qin, Xurong Lee, Marcus Wen Yao Zhou, Steve Jianrong |
| author_sort |
Qin, Xurong |
| title |
Nickel-Catalyzed Asymmetric Reductive Heck Cyclization of Aryl Halides to Afford Indolines |
| title_short |
Nickel-Catalyzed Asymmetric Reductive Heck Cyclization of Aryl Halides to Afford Indolines |
| title_full |
Nickel-Catalyzed Asymmetric Reductive Heck Cyclization of Aryl Halides to Afford Indolines |
| title_fullStr |
Nickel-Catalyzed Asymmetric Reductive Heck Cyclization of Aryl Halides to Afford Indolines |
| title_full_unstemmed |
Nickel-Catalyzed Asymmetric Reductive Heck Cyclization of Aryl Halides to Afford Indolines |
| title_sort |
nickel-catalyzed asymmetric reductive heck cyclization of aryl halides to afford indolines |
| publishDate |
2018 |
| url |
https://hdl.handle.net/10356/89028 http://hdl.handle.net/10220/44927 |
| _version_ |
1759853062640369664 |