Remote nucleophilic allylation by allylrhodium chain walking
Metal migration through a carbon chain is a versatile method for achieving remote functionalization. However, almost all known examples involve the overall net migration of alkylmetal species. Here, we report that allylrhodium species obtained from hydrorhodation of 1,3-dienes undergo chain walking...
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| Format: | Article |
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Wiley
2018
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| Online Access: | https://eprints.nottingham.ac.uk/53051/ |
| _version_ | 1848798866400346112 |
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| author | Groves, Alistair Martinez, Jose I. Smith, Joshua J. Lam, Hon Wai |
| author_facet | Groves, Alistair Martinez, Jose I. Smith, Joshua J. Lam, Hon Wai |
| author_sort | Groves, Alistair |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | Metal migration through a carbon chain is a versatile method for achieving remote functionalization. However, almost all known examples involve the overall net migration of alkylmetal species. Here, we report that allylrhodium species obtained from hydrorhodation of 1,3-dienes undergo chain walking toward esters, amides, or (hetero)arenes over distances of up to eight methylene units. The final, more highly conjugated allylrhodium species undergo nucleophilic allylation with aldehydes and an imine to give Z-homoallylic alcohols and amines, respectively. |
| first_indexed | 2025-11-14T20:26:35Z |
| format | Article |
| id | nottingham-53051 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| last_indexed | 2025-11-14T20:26:35Z |
| publishDate | 2018 |
| publisher | Wiley |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-530512020-05-04T19:46:04Z https://eprints.nottingham.ac.uk/53051/ Remote nucleophilic allylation by allylrhodium chain walking Groves, Alistair Martinez, Jose I. Smith, Joshua J. Lam, Hon Wai Metal migration through a carbon chain is a versatile method for achieving remote functionalization. However, almost all known examples involve the overall net migration of alkylmetal species. Here, we report that allylrhodium species obtained from hydrorhodation of 1,3-dienes undergo chain walking toward esters, amides, or (hetero)arenes over distances of up to eight methylene units. The final, more highly conjugated allylrhodium species undergo nucleophilic allylation with aldehydes and an imine to give Z-homoallylic alcohols and amines, respectively. Wiley 2018-07-13 Article PeerReviewed Groves, Alistair, Martinez, Jose I., Smith, Joshua J. and Lam, Hon Wai (2018) Remote nucleophilic allylation by allylrhodium chain walking. Chemistry - A European Journal . ISSN 0947-6539 allylation chain walking homogenous catalysis isomerization rhodium https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201803574 doi:10.1002/chem.201803574 doi:10.1002/chem.201803574 |
| spellingShingle | allylation chain walking homogenous catalysis isomerization rhodium Groves, Alistair Martinez, Jose I. Smith, Joshua J. Lam, Hon Wai Remote nucleophilic allylation by allylrhodium chain walking |
| title | Remote nucleophilic allylation by allylrhodium chain walking |
| title_full | Remote nucleophilic allylation by allylrhodium chain walking |
| title_fullStr | Remote nucleophilic allylation by allylrhodium chain walking |
| title_full_unstemmed | Remote nucleophilic allylation by allylrhodium chain walking |
| title_short | Remote nucleophilic allylation by allylrhodium chain walking |
| title_sort | remote nucleophilic allylation by allylrhodium chain walking |
| topic | allylation chain walking homogenous catalysis isomerization rhodium |
| url | https://eprints.nottingham.ac.uk/53051/ https://eprints.nottingham.ac.uk/53051/ https://eprints.nottingham.ac.uk/53051/ |