One-pot bifunctionalization of unactivated alkenes, P(O)-H compounds, and N-methoxypyridinium salts for the construction of -pyridyl alkylphosphonates

Cited 2 time in webofscience Cited 0 time in scopus
  • Hit : 80
  • Download : 0
beta-Pyridylphosphines consisting of vicinal pyridine and phosphine groups possess soft acceptor properties of phosphines and hard sigma-donor features of pyridines. An efficient method for the synthesis of -pyridyl alkylphosphonates was developed via a three-component reaction between P(O)-H compounds, alkenes and N-methoxypyridinium salts under mild conditions. The reaction is thought to occur by the addition of a phosphonyl radical to the alkene to form alkyl radical intermediate, which goes on to add to the N- N-methoxypyridinium salt. Solvation plays an important role and DFT calculations suggest that the solvation effect is critical in the first step where an alkyl radical intermediate is formed by coupling the phosphonyl radical and the alkene substrate. A plausible mechanism is proposed based on DFT calculations and this novel methodology is applied to a variety of heteroarenium salts and alkene substrates to prepare various synthetically and biologically important -pyridyl alkylphosphonates.
Publisher
ROYAL SOC CHEMISTRY
Issue Date
2018-09
Language
English
Article Type
Article
Keywords

C-H FUNCTIONALIZATION; ORGANOPHOSPHORUS COMPOUNDS; OXIDATIVE CYCLIZATION; HETEROAROMATIC BASES; RADICAL CYCLIZATION; CATALYZED-REACTIONS; CHIRAL P,N-LIGANDS; ARYLBORONIC ACIDS; TERMINAL ALKYNES; BOND ACTIVATION

Citation

ORGANIC CHEMISTRY FRONTIERS, v.5, no.17, pp.2595 - 2603

ISSN
2052-4129
DOI
10.1039/c8qo00689j
URI
http://hdl.handle.net/10203/245908
Appears in Collection
CH-Journal Papers(저널논문)
Files in This Item
There are no files associated with this item.
This item is cited by other documents in WoS
⊙ Detail Information in WoSⓡ Click to see webofscience_button
⊙ Cited 2 items in WoS Click to see citing articles in records_button

qr_code

  • mendeley

    citeulike


rss_1.0 rss_2.0 atom_1.0