Pot-Economy Autooxidative
Condensation of 2‑Aryl-2-lithio-1,3-dithianes
Version 2 2018-08-15, 20:17
Version 1 2018-01-26, 17:19
Posted on 2018-08-15 - 20:17
The
autoxidative condensation of 2-aryl-2-lithio-1,3-dithianes
is here reported. Treatment of 2-aryl-1,3-dithianes with n-BuLi in the absence of any electrophile leads to condensation of
three molecules of 1,3-dithianes and formation of highly functionalized
α-thioether ketones orthothioesters in 51–89% yields
upon air exposure. The method was further expanded to benzaldehyde
dithioacetals, affording corresponding orthothioesters and α-thioether
ketones in 48–97% yields. The experimental results combined
with density functional theory studies support a mechanism triggered
by the autoxidation of 2-aryl-2-lithio-1,3-dithianes to yield a highly
reactive thioester that undergoes condensation with two other molecules
of 2-aryl-2-lithio-1,3-dithiane.
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Vale, João
R.; Rimpiläinen, Tatu; Sievänen, Elina; Rissanen, Kari; A. M. Afonso, Carlos; Candeias, Nuno R. (2018). Pot-Economy Autooxidative
Condensation of 2‑Aryl-2-lithio-1,3-dithianes. ACS Publications. Collection. https://doi.org/10.1021/acs.joc.7b02896
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AUTHORS (6)
JV
João
R. Vale
TR
Tatu Rimpiläinen
ES
Elina Sievänen
KR
Kari Rissanen
CA
Carlos A. M. Afonso
NC
Nuno R. Candeias