Highly efficient synthesis of 1,1-difluoro-2-substituted-1,3-dienes and dienynes from gem-difluorohomoallenyl bromide via palladium-catalyzed cross-coupling reactions.
[reaction: see text] A stable gem-difluoroallenylindium 1 is readily transformed to a potentially bifunctional electrophile 2, which can then undergo a transition-metal-promoted isomerization-cross-coupling cascade to yield diene 3 and dienyne 4 in very high yields.
Shen
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Department of Chemistry and Biochemistry, University of Massachusetts Dartmouth, North Dartmouth, Massachusetts 02747, USA.
Hammond
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