Catalytic CH Bond Addition of Pyridines to Allenes by a Rare-Earth Catalyst
The catalytic CH addition of pyridines to allenes has been achieved for the first time by using a half‐sandwich scandium catalyst, thus constituting a straightforward and atom‐economical route for the synthesis of alkenylated pyridine derivatives. The reaction proceeded regio‐ and stereoselectively...
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| Published in | Chemistry : a European journal Vol. 21; no. 23; pp. 8394 - 8398 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
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Weinheim
WILEY-VCH Verlag
01.06.2015
WILEY‐VCH Verlag Wiley |
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| Abstract | The catalytic CH addition of pyridines to allenes has been achieved for the first time by using a half‐sandwich scandium catalyst, thus constituting a straightforward and atom‐economical route for the synthesis of alkenylated pyridine derivatives. The reaction proceeded regio‐ and stereoselectively, affording a new family of alkenylated pyridine compounds which are otherwise difficult to synthesize. A cationic Sc‐η2‐pyridyl species was isolated and confirmed to be a key catalyst species in this transformation.
Keep it allene: Half‐sandwich scandium dialkyls combined with a borate compound act as an efficient catalyst for the CH bond addition of pyridines to various terminal allenes, leading to formation of a new family of alkenylated pyridine derivatives in high yields and excellent regio‐ and stereoselectivity. A cationic scandium pyridyl species (see scheme) was isolated and confirmed to be a key active catalyst species. |
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| AbstractList | The catalytic C-H addition of pyridines to allenes has been achieved for the first time by using a half-sandwich scandium catalyst, thus constituting a straightforward and atom-economical route for the synthesis of alkenylated pyridine derivatives. The reaction proceeded regio- and stereoselectively, affording a new family of alkenylated pyridine compounds which are otherwise difficult to synthesize. A cationic Sc-η(2) -pyridyl species was isolated and confirmed to be a key catalyst species in this transformation.The catalytic C-H addition of pyridines to allenes has been achieved for the first time by using a half-sandwich scandium catalyst, thus constituting a straightforward and atom-economical route for the synthesis of alkenylated pyridine derivatives. The reaction proceeded regio- and stereoselectively, affording a new family of alkenylated pyridine compounds which are otherwise difficult to synthesize. A cationic Sc-η(2) -pyridyl species was isolated and confirmed to be a key catalyst species in this transformation. The catalytic CH addition of pyridines to allenes has been achieved for the first time by using a half‐sandwich scandium catalyst, thus constituting a straightforward and atom‐economical route for the synthesis of alkenylated pyridine derivatives. The reaction proceeded regio‐ and stereoselectively, affording a new family of alkenylated pyridine compounds which are otherwise difficult to synthesize. A cationic Sc‐η 2 ‐pyridyl species was isolated and confirmed to be a key catalyst species in this transformation. The catalytic C--H addition of pyridines to allenes has been achieved for the first time by using a half-sandwich scandium catalyst, thus constituting a straightforward and atom-economical route for the synthesis of alkenylated pyridine derivatives. The reaction proceeded regio- and stereoselectively, affording a new family of alkenylated pyridine compounds which are otherwise difficult to synthesize. A cationic Sc- eta super(2)-pyridyl species was isolated and confirmed to be a key catalyst species in this transformation. Keep it allene: Half-sandwich scandium dialkyls combined with a borate compound act as an efficient catalyst for the C--H bond addition of pyridines to various terminal allenes, leading to formation of a new family of alkenylated pyridine derivatives in high yields and excellent regio- and stereoselectivity. A cationic scandium pyridyl species (see scheme) was isolated and confirmed to be a key active catalyst species. The catalytic CH addition of pyridines to allenes has been achieved for the first time by using a half‐sandwich scandium catalyst, thus constituting a straightforward and atom‐economical route for the synthesis of alkenylated pyridine derivatives. The reaction proceeded regio‐ and stereoselectively, affording a new family of alkenylated pyridine compounds which are otherwise difficult to synthesize. A cationic Sc‐η2‐pyridyl species was isolated and confirmed to be a key catalyst species in this transformation. Keep it allene: Half‐sandwich scandium dialkyls combined with a borate compound act as an efficient catalyst for the CH bond addition of pyridines to various terminal allenes, leading to formation of a new family of alkenylated pyridine derivatives in high yields and excellent regio‐ and stereoselectivity. A cationic scandium pyridyl species (see scheme) was isolated and confirmed to be a key active catalyst species. The catalytic CH addition of pyridines to allenes has been achieved for the first time by using a half-sandwich scandium catalyst, thus constituting a straightforward and atom-economical route for the synthesis of alkenylated pyridine derivatives. The reaction proceeded regio- and stereoselectively, affording a new family of alkenylated pyridine compounds which are otherwise difficult to synthesize. A cationic Sc-(2)-pyridyl species was isolated and confirmed to be a key catalyst species in this transformation. The catalytic C-H addition of pyridines to allenes has been achieved for the first time by using a half-sandwich scandium catalyst, thus constituting a straightforward and atom-economical route for the synthesis of alkenylated pyridine derivatives. The reaction proceeded regio- and stereoselectively, affording a new family of alkenylated pyridine compounds which are otherwise difficult to synthesize. A cationic Sc-η(2) -pyridyl species was isolated and confirmed to be a key catalyst species in this transformation. |
| Author | Hou, Zhaomin Wang, Baoli Song, Guoyong Nishiura, Masayoshi |
| Author_xml | – sequence: 1 givenname: Guoyong surname: Song fullname: Song, Guoyong organization: Organometallic Chemistry Laboratory and RIKEN Center for Sustainable Resource Science, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198 (Japan) – sequence: 2 givenname: Baoli surname: Wang fullname: Wang, Baoli organization: Organometallic Chemistry Laboratory and RIKEN Center for Sustainable Resource Science, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198 (Japan) – sequence: 3 givenname: Masayoshi surname: Nishiura fullname: Nishiura, Masayoshi organization: Organometallic Chemistry Laboratory and RIKEN Center for Sustainable Resource Science, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198 (Japan) – sequence: 4 givenname: Zhaomin surname: Hou fullname: Hou, Zhaomin email: houz@riken.jp organization: Organometallic Chemistry Laboratory and RIKEN Center for Sustainable Resource Science, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198 (Japan) |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/25899713$$D View this record in MEDLINE/PubMed |
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| Keywords | ACTIVATION ALKYL COMPLEXES REACTIVITY scandium POLYMERIZATION SELECTIVE ALKENYLATION ALLYLATIONS alkenylation allenes pyridines C-H addition INSERTION REACTIONS COPOLYMERIZATION DERIVATIVES CH addition |
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| Snippet | The catalytic CH addition of pyridines to allenes has been achieved for the first time by using a half‐sandwich scandium catalyst, thus constituting a... The catalytic CH addition of pyridines to allenes has been achieved for the first time by using a half-sandwich scandium catalyst, thus constituting a... The catalytic C-H addition of pyridines to allenes has been achieved for the first time by using a half-sandwich scandium catalyst, thus constituting a... The catalytic C--H addition of pyridines to allenes has been achieved for the first time by using a half-sandwich scandium catalyst, thus constituting a... |
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| SubjectTerms | alkenylation allenes Bonding Catalysis Catalysts Cationic Chemistry Chemistry, Multidisciplinary CH addition Derivatives Physical Sciences Pyridines Rare earth metals Scandium Science & Technology |
| Title | Catalytic CH Bond Addition of Pyridines to Allenes by a Rare-Earth Catalyst |
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