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...
| Main Authors: | , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
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2018
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| Online Access: | https://hdl.handle.net/10356/89028 http://hdl.handle.net/10220/44927 |
| _version_ | 1826110079371313152 |
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| author | Qin, Xurong Lee, Marcus Wen Yao Zhou, Steve Jianrong |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Qin, Xurong Lee, Marcus Wen Yao Zhou, Steve Jianrong |
| author_sort | Qin, Xurong |
| collection | NTU |
| 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. |
| first_indexed | 2024-10-01T02:28:56Z |
| format | Journal Article |
| id | ntu-10356/89028 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T02:28:56Z |
| publishDate | 2018 |
| record_format | dspace |
| spelling | ntu-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 |
| spellingShingle | Asymmetric Catalysis Cyclization Qin, Xurong Lee, Marcus Wen Yao Zhou, Steve Jianrong Nickel-Catalyzed Asymmetric Reductive Heck Cyclization of Aryl Halides to Afford Indolines |
| title | 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_short | 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 |
| topic | Asymmetric Catalysis Cyclization |
| url | https://hdl.handle.net/10356/89028 http://hdl.handle.net/10220/44927 |
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