90921-35-0Relevant articles and documents
Nucleophilic Amination and Etherification of Aryl Alkyl Thioethers
Wang, Xia,Tang, Yue,Long, Cheng-Yu,Dong, Wen-Ke,Li, Chenchen,Xu, Xinhua,Zhao, Wanxiang,Wang, Xue-Qiang
supporting information, p. 4749 - 4753 (2018/08/23)
A transition-metal-free protocol capable of synthesizing diarylated aniline derivatives is reported. This method could be further employed to prepare aryl alkyl ethers. A wide range of thioethers, anilines, as well as alcohols were tolerated thanks to the mild reaction conditions. The strength of our method was demonstrated by performing a gram-scale reaction (20 mmol) followed by conversion of the nitrile group into synthetically useful aldehyde, ketone, and carboxylic acid.
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.