Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 24, Issue 51, Pages 13432-13436Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201803574
Keywords
allylation; chain walking; homogeneous catalysis; isomerization; rhodium
Categories
Funding
- Engineering and Physical Sciences Research Council [EP/M50810X/1, EP/K504348/1]
- Basque Country government
- Leverhulme Trust [RPG-2016-341]
- GlaxoSmithKline
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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 with an imine to give Z-homoallylic alcohols and amines, respectively.
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