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Pd(0)-catalyzed selective [2 + 2 + 2] cycloaddition of dimethyl nona-2,7-diyne-1,9-dioate derivatives with dimethyl acetylenedicarboxylate

โœ Scribed by Yoshihiko Yamamoto; Asako Nagata; Kenji Itoh

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
245 KB
Volume
40
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

In the presence of 2.5 mol % of Pd2(dba) 3 and 5 tool % ofPPh 3, nearly eqcimolar mnounts of dimathyl nona-2,7-diyne-1,9-dioate derivatives and dimethy! acetylenedicarboxylate (DMAD) were reacted in toluene at 110 "C to give indan, phthalin, a~d isoindoline derivatives selectively in moderate to good yield,. The compe~ hmno-t~uplings of both the diynedlesters and DMAD were mmplew.ly suplnt~sed. The ester groe~ on the alkyne terminus plays an important role; the corresponding diynaliket~e e=d diynemmmmer gave unsatisfactory results. The Ixesent Pd(0)-catalyzed cyclminzdmm was further extended to the inUamok=~ [2 + 2 + 2] cycloaddition of a triynediester.

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