1260224-35-8Relevant articles and documents
Iron-catalysed enantioconvergent Suzuki-Miyaura cross-coupling to afford enantioenriched 1,1-diarylalkanes
Tyrol, Chet C.,Yone, Nang S.,Gallin, Connor F.,Byers, Jeffery A.
supporting information, p. 14661 - 14664 (2020/12/02)
The first stereoconvergent Suzuki-Miyaura cross-coupling reaction was developed to afford enantioenriched 1,1-diarylalkanes. An iron-based complex containing a chiral cyanobis(oxazoline) ligand framework was best to obtain enantioenriched 1,1-diarylalkanes from cross-coupling reactions between unactivated aryl boronic esters and benzylic chlorides. Enhanced yields were obtained when 1,3,5-trimethoxybenzene was used as an additive, which is hypothesized to extend the lifetime of the iron-based catalyst. Exceptional enantioselectivities were obtained with challenging ortho-substituted benzylic chlorides. This journal is
Catalytic asymmetric hydrogenation using a [2.2]paracyclophane based chiral 1,2,3-triazol-5-ylidene-Pd complex under ambient conditions and 1 atmosphere of H2
Dasgupta, Ayan,Ramkumar, Venkatachalam,Sankararaman, Sethuraman
, p. 21558 - 21561 (2015/03/30)
Chiral 1,2,3-triazol-5-ylidene-Pd complexes with the planar chiral [2.2]paracyclophane wing tip group have been synthesized and structurally characterized. The complex with a labile acetonitrile co-ligand is an excellent catalyst for chemoselective hydrogenation of alkynes and alkenes and enantioselective hydrogenation of prochiral alkenes at ambient conditions and 1.0 atmosphere of H2.
Nickel-catalyzed cross-couplings of benzylic pivalates with arylboroxines: Stereospecific formation of diarylalkanes and triarylmethanes
Zhou, Qi,Srinivas, Harathi D.,Dasgupta, Srimoyee,Watson, Mary P.
supporting information, p. 3307 - 3310 (2013/04/23)
We have developed a stereospecific nickel-catalyzed cross-coupling of benzylic pivalates with arylboroxines. The success of this reaction relies on the use of Ni(cod)2 as the catalyst and NaOMe as a uniquely effective base. This reaction has broad scope with respect to the arylboroxine and benzylic pivalate, enabling the synthesis of a variety of diarylalkanes and triarylmethanes in good to excellent yields and ee's.
Functional-group-tolerant, nickel-catalyzed cross-coupling reaction for enantioselective construction of tertiary methyl-bearing stereocenters
Wisniewska, Hanna M.,Swift, Elizabeth C.,Jarvo, Elizabeth R.
, p. 9083 - 9090 (2013/07/26)
The first Negishi nickel-catalyzed stereospecific cross-coupling reaction of secondary benzylic esters is reported. A series of traceless directing groups is evaluated for ability to promote cross-coupling with dimethylzinc. Esters with a chelating thioether derived from commercially available 2-(methylthio)acetic acid are most effective. The products are formed in high yield and with excellent stereospecificity. A variety of functional groups are tolerated in the reaction including alkenes, alkynes, esters, amines, imides, and O-, S-, and N-heterocycles. The utility of this transformation is highlighted in the enantioselective synthesis of a retinoic acid receptor agonist and a fatty acid amide hydrolase inhibitor.
Carboxy-directed asymmetric hydrogenation of 1,1-diarylethenes and 1,1-dialkylethenes
Song, Song,Zhu, Shou-Fei,Yu, Yan-Bo,Zhou, Qi-Lin
supporting information, p. 1556 - 1559 (2013/04/24)
Carboxy marks the spot: A carboxy-directed asymmetric hydrogenation of 1,1-diarylethenes and 1,1-dialkylethenes with chiral iridium/spiro phosphine-oxazoline catalysts has been developed. A wide range of chiral diarylethanes and chiral γ-methyl fatty acids were synthesized with excellent enantioselectivity (see scheme). Copyright
Stereospecific nickel-catalyzed cross-coupling reactions of alkyl ethers: Enantioselective synthesis of diarylethanes
Taylor, Buck L. H.,Swift, Elizabeth C.,Waetzig, Joshua D.,Jarvo, Elizabeth R.
, p. 389 - 391 (2011/04/16)
Secondary benzylic ethers undergo stereospecific substitution reactions with Grignard reagents in the presence of nickel catalysts. Reactions proceed with inversion of configuration and high stereochemical fidelity. This reaction allows for facile enantio
