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Reductive Coupling of Aldehydes by H 2 S in Aqueous Solutions, a CC Bond Forming Reaction of Prebiotic Interest
Author(s) -
Kajjout Mohammed,
Hebting Yanek,
Albrecht Pierre,
Adam Pierre
Publication year - 2012
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201100124
Subject(s) - chemistry , glyoxylic acid , aqueous solution , abiogenesis , prebiotic , coupling reaction , reductive elimination , conjugated system , organic chemistry , photochemistry , astrobiology , catalysis , biochemistry , physics , polymer
We report here a novel reductive coupling reaction of conjugated, non‐ or poorly enolizable aldehydes induced by H 2 S and operative in aqueous solutions under prebiotically relevant conditions. This reaction leads from retinal to β ‐carotene, and from benzylic aldehydes to the corresponding diarylethylenes. This novel reaction also opens a new potentially prebiotic pathway leading from glyoxylic acid to various compounds that are involved in the reductive tricarboxylic acid cycle. This CC bond forming reaction of prebiotic interest might have been operative, notably, in the sulfide‐rich environments of hydrothermal vents, which have been postulated as possible sites for the first steps of organic chemical evolution.