V. Gevorgyan et al., Synthesis of indenols and indanones via catalytic cyclic vinylpalladation of aromatic aldehydes, TETRAHEDR L, 40(21), 1999, pp. 4089-4092
o-Bromobenzaldehyde 1, in the presence of a palladium catalyst, smoothly un
derwent consecutive intermolecular carbopalladation with internal alkynes 2
and then intramolecular nucleophilic vinylpalladation of the aldehyde func
tion to produce the indenol derivatives 4 in high yields. Further heating o
f 4 under more elevated temperature caused complete isomerization to the co
rresponding indanones 8. A mechanism for this nucleophilic vinylpalladation
of aromatic aldehydes is proposed. (C) 1999 Elsevier Science Ltd. All righ
ts reserved.