90921-35-0Relevant articles and documents
Metal-Free Etherification of Aryl Methyl Ether Derivatives by C-OMe Bond Cleavage
Wang, Xueqiang,Li, Chenchen,Wang, Xia,Wang, Qingli,Dong, Xiu-Qin,Duan, Abing,Zhao, Wanxiang
, p. 4267 - 4272 (2018/07/29)
A general and efficient protocol was developed for the synthesis of aryl alkyl ethers through metal-free C-OMe bond cleavage under mild reaction conditions. This process displays a wide scope of methoxyarenes and alcohols, including primary, secondary, and tertiary alcohols, as well as natural products, pharmaceuticals, and biologically active alcohols. DFT calculations and experimental results simultaneously confirm that a potassium ion plays a critical role in the activation of methoxy group via binding with the nitrile and provide support for an SNAr mechanism.
Exploiting ancillary ligation to enable nickel-catalyzed c-o cross-couplings of aryl electrophiles with aliphatic alcohols
MacQueen, Preston M.,Tassone, Joseph P.,Diaz, Carlos,Stradiotto, Mark
supporting information, p. 5023 - 5027 (2018/04/24)
The use of (L)Ni(o-tolyl)Cl precatalysts (L = PAd-DalPhos or CyPAd-DalPhos) enables the C(sp2)-O cross-coupling of primary, secondary, or tertiary aliphatic alcohols with (hetero)aryl electrophiles, including unprecedented examples of such nickel-catalyzed transformations employing (hetero)aryl chlorides, sulfonates, and pivalates. In addition to offering a competitive alternative to palladium catalysis, this work establishes the feasibility of utilizing ancillary ligation as a complementary means of promoting challenging nickel-catalyzed C(sp2)-O cross-couplings, without recourse to precious-metal photoredox catalytic methods.
Dynamic kinetic asymmetric synthesis of substituted pyrrolidines from racemic cyclopropanes and aldimines: Reaction development and mechanistic insights
Parsons, Andrew T.,Smith, Austin G.,Neel, Andrew J.,Johnson, Jeffrey S.
supporting information; experimental part, p. 9688 - 9692 (2010/09/06)
An enantioselective preparation of 2,5-cis-disubstituted pyrrolidines has been achieved via a dynamic kinetic asymmetric transformation (DyKAT) of racemic donor-acceptor cyclopropanes and (E)-aldimines. Mechanistic studies suggest that isomerization of the aldimine or resultant iminium to the Z geometry is not a pathway that furnishes the observed 2,5-cis-disubstituted products.
