ArticleAngewandte Chemie (International ed. in English)2016
Practical Organocatalytic Synthesis of Functionalized Non-C2-Symmetrical Atropisomeric Biaryls.
Article in Angewandte Chemie (International ed. in English), 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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Who cites it
17 citing papers in PubMed.
- Cyclic sulfone ring remodeling enables molecular shape diversity-oriented synthesis of privileged biaryl and oligoaryl motifs.Nature communications · 2026Article
- Fluorinated Para-Quinone Monoacetal: Versatile Reactivity for Constructing Functionalized Scaffolds.Chemistry, an Asian journal · 2025Article
- Bayesian optimization-driven parallel-screening of multiple parameters for the flow synthesis of biaryl compounds.Communications chemistry · 2022Article
- Article
- Cu(i) catalysis for selective condensation/bicycloaromatization of two different arylalkynes: direct and general construction of functionalized C-N axial biaryl compounds.Chemical science · 2021Article
- Peptide-Catalyzed Fragment Couplings that Form Axially Chiral Non-CAngewandte Chemie (International ed. in English) · 2020Article
- Catalytic Atroposelective Synthesis ofJournal of the American Chemical Society · 2020Article
- Regioselective Oxidative Arylation of Fluorophenols.Angewandte Chemie (International ed. in English) · 2019Article
- Conversion of two stereocenters to one or two chiral axes: atroposelective synthesis of 2,3-diarylbenzoindoles.Chemical science · 2019Article
- Practical access to axially chiral sulfonamides and biaryl amino phenols via organocatalytic atroposelective N-alkylation.Nature communications · 2019Article
- Practical and Scalable Kinetic Resolution of BINOLs Mediated by a Chiral Counterion.Angewandte Chemie (International ed. in English) · 2019Article
- Base-promoted lipase-catalyzed kinetic resolution of atropisomeric 1,1'-biaryl-2,2'-diols.RSC advances · 2019Article
- Why do thioureas and squaramides slow down the Ireland-Claisen rearrangement?Beilstein journal of organic chemistry · 2019Article
- Enantioselective [3+3] atroposelective annulation catalyzed by N-heterocyclic carbenes.Nature communications · 2018Article
- Catalytic enantioselective synthesis of atropisomeric biaryls by a cation-directed O-alkylation.Nature chemistry · 2017Article
- Organocatalytic atroposelective synthesis of axially chiral styrenes.Nature communications · 2017Article
- Symmetry in Cascade Chirality-Transfer Processes: A Catalytic Atroposelective Direct Arylation Approach to BINOL Derivatives.Journal of the American Chemical Society · 2016Article
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6 authors.
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Abstract
An organic acid catalyzed direct arylation of aromatic C(sp(2))-H bonds in phenols and naphthols for the preparation of 1,1'-linked functionalized biaryls was developed. The products are non-C2-symmetrical, atropoisomeric, and represent previously untapped chemical space. Overall this transformation is operationally simple, does not require an external oxidant, is readily scaled up (up to 98 mmol), and the structurally diverse 2,2'-dihydroxy biaryl (i.e., BINOL-type), as well as 2-amino-2'-hydroxy products (i.e., NOBIN-type) are formed with complete regioselectivity. Density-functional calculations suggest that the quinone and imino-quinone monoacetal coupling partners are exclusively arylated at their α-position by an asynchronous [3,3]-sigmatropic rearrangement of a mixed acetal species which is formed in situ under the reaction conditions.
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