98689-34-0Relevant articles and documents
Photoinduced electron-transfer reactions of arylmethyl-substituted 14 group compounds: Photoarylmethylation and photooxygenation
Tamai,Mizuno,Hashida,Otsuji
, p. 3747 - 3754 (1993)
Photoreactions of arylmethylsilanes, -germane, and -stannane with 1,4- dicyanonaphthalene (DCN) and 9, 10-dicyanoanthracene (DCA) were studied under various conditions. The arylmethylation of DCN and DCA occurred in the photoreaction under nitrogen atmosphere, whereas the oxygenation of the arylmethyl organometallic compounds occurred in the photoreaction under oxygen atmosphere. Key intermediates in these reactions in acetonitrile were radical ions which were generated via photoinduced electron transfer from the arylmethyl organometallic compounds to the excited singlet of DCN or DCA. The cleavage of the carbon-metal bond of the radical cations of the arylmethyl compounds resulted in the formation of arylmethyl radicals. The radicals reacted then with the radical anions of DCN and DCA to produce the arylmethylated compounds or reacted with oxygen to produce the oxygenated compounds. The efficiency of the photoreactions was affected by solvents and added materials to the reaction systems. In the photoreactions in benzene, the exciplexes of the type 1[A-ArCH2MR3]* or the triplexes of the type [A-C6H6-ArCH2MR3]* (A=DCN, DCA) were involved as intermediates. The reactivity features of the photoreactions are discussed.
Lewis Basic Salt-Promoted Organosilane Coupling Reactions with Aromatic Electrophiles
Bandar, Jeffrey S.,Reidl, Tyler W.
supporting information, p. 11939 - 11945 (2021/08/20)
Lewis basic salts promote benzyltrimethylsilane coupling with (hetero)aryl nitriles, sulfones, and chlorides as a new route to 1,1-diarylalkanes. This method combines the substrate modularity and selectivity characteristic of cross-coupling with the practicality of a base-promoted protocol. In addition, a Lewis base strategy enables a complementary scope to existing methods, employs stable and easily prepared organosilanes, and achieves selective arylation in the presence of acidic functional groups. The utility of this method is demonstrated by the synthesis of pharmaceutical analogues and its use in multicomponent reactions.
Set Photochemical Reactions between 1,4-Naphthalenedicarbonitrile and Benzylic Donors. Medium Effects
Fasani, E.,d'Alessandro, N.,Albini, A.,Mariano, P. S.
, p. 829 - 835 (2007/10/02)
The electron transfer induced photochemical reactions 1,4-naphthalenedicarbonitrile (NDN) with toluene (1a), diphenylmethane (1b), p-methoxytoluene (1c), and benzyltrimethylsilane (1d) in MeOH-MeCN and 0.1 M KOH-MeOH-MeCN were examined.The results were compared with those of reactions occurring in neat MeCN.Under the former conditions, the cation radical derived from 1a undergoes deprotonation after diffusion from (rather than within) the geminate ion pair (as in MeCN).The formed benzyl radical abstracts a hydrogen from MeOH leading to hydroxymethylation of NDN competitively with its benzylation.Under basis conditions MeO(-) adds to 1a(+.) yielding 1c.The reaction of 1b in MeOH-MeCN and 0.1 M KOH-MeOH-MeCN is similar to that of 1a.However, in the reaction of 1c under these conditions, the arene cation radical undergoes deprotonation out of cage.Finally, desilylation of the cation radical from 1d is a fast process occurring from the geminate pair in all the media explored.
Photoarylmethylation of 1,4-Dicyanonaphthalene by Use of Group 14 Organometallic Compounds
Mizuno, Kazuhiko,Terasaka, Kiyotaro,Yasueda, Masahiro,Otsuji, Yoshio
, p. 145 - 148 (2007/10/02)
The photoreaction of 1,4-dicyanonaphthalene (DCN) with arylmethylsilanes, germane, and stannane in polar solvents gave the arylmethylated products of DCN in high yields.The fluorescence of DCN was efficiently quenched both in polar and nonpolar solvents b
