Pivalophenone imine as a benzonitrile surrogate for directed C–H bond functionalization
Pivalophenone N–H imine has been found to serve as a prominent substrate for directed C–H alkylation and arylation reactions with alkyl bromides and aryl chlorides, respectively, under cobalt–N-heterocyclic carbene (NHC) catalysis. Unlike the case of the parent pivalophenone imine, the increased ste...
| Main Authors: | , |
|---|---|
| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2018
|
| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/86808 http://hdl.handle.net/10220/44261 |
| _version_ | 1811694823657177088 |
|---|---|
| author | Xu, Wengang Yoshikai, Naohiko |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Xu, Wengang Yoshikai, Naohiko |
| author_sort | Xu, Wengang |
| collection | NTU |
| description | Pivalophenone N–H imine has been found to serve as a prominent substrate for directed C–H alkylation and arylation reactions with alkyl bromides and aryl chlorides, respectively, under cobalt–N-heterocyclic carbene (NHC) catalysis. Unlike the case of the parent pivalophenone imine, the increased steric bulk of the resulting ortho-substituted pivalophenone imines allows them to undergo clean imine-to-nitrile conversion under peroxide photolysis or aerobic copper catalysis conditions. Overall, these two-step transformations offer convenient synthetic methods for ortho-functionalized benzonitriles. |
| first_indexed | 2024-10-01T07:13:42Z |
| format | Journal Article |
| id | ntu-10356/86808 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T07:13:42Z |
| publishDate | 2018 |
| record_format | dspace |
| spelling | ntu-10356/868082023-02-28T19:34:18Z Pivalophenone imine as a benzonitrile surrogate for directed C–H bond functionalization Xu, Wengang Yoshikai, Naohiko School of Physical and Mathematical Sciences C–H Bond Functionalization Arylation Reactions Pivalophenone N–H imine has been found to serve as a prominent substrate for directed C–H alkylation and arylation reactions with alkyl bromides and aryl chlorides, respectively, under cobalt–N-heterocyclic carbene (NHC) catalysis. Unlike the case of the parent pivalophenone imine, the increased steric bulk of the resulting ortho-substituted pivalophenone imines allows them to undergo clean imine-to-nitrile conversion under peroxide photolysis or aerobic copper catalysis conditions. Overall, these two-step transformations offer convenient synthetic methods for ortho-functionalized benzonitriles. MOE (Min. of Education, S’pore) Published version 2018-01-08T06:40:31Z 2019-12-06T16:29:21Z 2018-01-08T06:40:31Z 2019-12-06T16:29:21Z 2017 Journal Article Xu, W., & Yoshikai, N. (2017). Pivalophenone imine as a benzonitrile surrogate for directed C–H bond functionalization. Chemical Science, 8(8), 5299-5304. 2041-6520 https://hdl.handle.net/10356/86808 http://hdl.handle.net/10220/44261 10.1039/C7SC01732D en Chemical Science © 2017 The Author(s) (published by Royal Society of Chemistry). This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. 6 p. application/pdf |
| spellingShingle | C–H Bond Functionalization Arylation Reactions Xu, Wengang Yoshikai, Naohiko Pivalophenone imine as a benzonitrile surrogate for directed C–H bond functionalization |
| title | Pivalophenone imine as a benzonitrile surrogate for directed C–H bond functionalization |
| title_full | Pivalophenone imine as a benzonitrile surrogate for directed C–H bond functionalization |
| title_fullStr | Pivalophenone imine as a benzonitrile surrogate for directed C–H bond functionalization |
| title_full_unstemmed | Pivalophenone imine as a benzonitrile surrogate for directed C–H bond functionalization |
| title_short | Pivalophenone imine as a benzonitrile surrogate for directed C–H bond functionalization |
| title_sort | pivalophenone imine as a benzonitrile surrogate for directed c h bond functionalization |
| topic | C–H Bond Functionalization Arylation Reactions |
| url | https://hdl.handle.net/10356/86808 http://hdl.handle.net/10220/44261 |
| work_keys_str_mv | AT xuwengang pivalophenoneimineasabenzonitrilesurrogatefordirectedchbondfunctionalization AT yoshikainaohiko pivalophenoneimineasabenzonitrilesurrogatefordirectedchbondfunctionalization |