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Nickel-catalyzed intramolecular allylation of alkenes and alkynes coupled with β-elimination or carbonylation

✍ Scribed by Wolfgang Oppolzer; Manuel Bedoya-Zurita; Christopher Y. Switzer

Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
319 KB
Volume
29
Category
Article
ISSN
0040-4039

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✦ Synopsis

Intramolecular allylations, combined with either fl-eliminations (1 --+ 2) or carbonylations (J_Q + 12 + 12, x'aand u+ 19 + m were catalyzed by Pt(PPh3)4, Ni(COD)/dppb, or Ni(C0)3PPh3, respectively. Pd"-catalyzed conversion of allylic acetates, alcohols and acetals A, B + F (Scheme 1) exemplifies part of a new stereospecific methodology leading to an array of monocylic or annulated carbo-and heterocyclic systems. The experimental results are consistent with an alkene insertion into a u-allyl-(D + E) or r-allyl-palladium unit (C + E ) and a subsequent p-elimination which regenerates Pd" ').

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## Abstract Transition‐metal‐catalyzed coupling of two different CC π components through a metallacycle intermediate is a highly atom economical method to construct CC bonds in organic synthesis. The metal‐catalyzed coupling of an alkene and alkyne generally gives an Alder‐ene or reductive coupli