TY - JOUR
T1 - Reactions of HDDA-Derived Benzynes with Sulfides
T2 - Mechanism, Modes, and Three-Component Reactions
AU - Chen, Junhua
AU - Palani, Vignesh
AU - Hoye, Thomas R.
PY - 2016/4/20
Y1 - 2016/4/20
N2 - We report here reactions of alkyl sulfides with benzynes thermally generated by the hexadehydro-Diels-Alder (HDDA) cycloisomerization. The initially produced 1,3-betaine (o-sulfonium/aryl carbanion) undergoes intramolecular proton transfer to generate a more stable S-aryl sulfur ylide. This can react in various manners, including engaging weak acids (HA) in the reaction medium. This can produce transient ion pairs ArSR2+A- that proceed to the products ArSR + RA. When cyclic sulfides are used, A- opens the ring and is incorporated into the product, an outcome that constitutes a versatile, three-component coupling process.
AB - We report here reactions of alkyl sulfides with benzynes thermally generated by the hexadehydro-Diels-Alder (HDDA) cycloisomerization. The initially produced 1,3-betaine (o-sulfonium/aryl carbanion) undergoes intramolecular proton transfer to generate a more stable S-aryl sulfur ylide. This can react in various manners, including engaging weak acids (HA) in the reaction medium. This can produce transient ion pairs ArSR2+A- that proceed to the products ArSR + RA. When cyclic sulfides are used, A- opens the ring and is incorporated into the product, an outcome that constitutes a versatile, three-component coupling process.
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U2 - 10.1021/jacs.6b01025
DO - 10.1021/jacs.6b01025
M3 - Article
C2 - 27010747
AN - SCOPUS:84964680275
VL - 138
SP - 4318
EP - 4321
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 13
ER -