Visible-Light-Induced Cascade Reaction of Isocyanides
and N‑Arylacrylamides with Diphenylphosphine
Oxide via Radical C–P and C–C Bond Formation
Version 2 2016-10-03, 15:36
Version 1 2016-09-28, 16:05
Posted on 2016-09-28 - 00:00
An effective photoredox-mediated
tandem phosphorylation/cyclization
reaction of diphenylphosphine oxide with three types of radical acceptors
leads to P(O)Ph2-containing phenanthridines, isoquinolines,
and indolin-2-ones by formation of both C–P and C–C
bonds. [Ir(ppy)2(dtbpy)]PF6 (1 mol %) was used
as the catalyst, CsF or Cs2CO3 as the base,
and K2S2O8 as the oxidant. A series
of functional groups can be tolerated at room temperature. Moderate
to good yields were generated.
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Li, Chun-Xiao; Tu, De-Shuang; Yao, Rui; Yan, Hong; Lu, Chang-Sheng (2016). Visible-Light-Induced Cascade Reaction of Isocyanides
and N‑Arylacrylamides with Diphenylphosphine
Oxide via Radical C–P and C–C Bond Formation. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.6b02413
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AUTHORS (5)
CL
Chun-Xiao Li
DT
De-Shuang Tu
RY
Rui Yao
HY
Hong Yan
CL
Chang-Sheng Lu
KEYWORDS
Iroxidantseriesroom temperaturemolK 2 S 2 O 8yielddtbpyDiphenylphosphine OxideModerateCsFVisible-Light-Induced Cascade ReactionFormationacceptortypeIsocyanidetandemformationcatalystdiphenylphosphine oxidephotoredox-mediatedBondindolin -2-onesRadicalphenanthridinephosphorylationCs 2 CO 3Arylacrylamideisoquinolinebond