- Synthesis of Chiral 3,3?-Disubstituted (S)-BINOL Derivatives via the Kumada and Suzuki Coupling and Their Antibacterial Activity
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Abstract: A new series of 3,3?-disubstituted chiral (S)-BINOL derivatives 6a–6k has been synthesized viathe Kumada and Suzuki–Miyaura coupling reactions using (S)-BINOL as the initial compound. The Kumada coupling has beenfound to be superior in terms of
- Ankireddy, A. Reddy,Paidikondala,Syed,Gundla,Reddy, Ch. Venkata Ramana,Ganapathi
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- Enantioselective Ni-Catalyzed Electrochemical Synthesis of Biaryl Atropisomers
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A scalable enantioselective nickel-catalyzed electrochemical reductive homocoupling of aryl bromides has been developed, affording enantioenriched axially chiral biaryls in good yield under mild conditions using electricity as a reductant in an undivided cell. Common metal reductants such as Mn or Zn powder resulted in significantly lower yields in the absence of electric current under otherwise identical conditions, underscoring the enhanced reactivity provided by the combination of transition metal catalysis and electrochemistry.
- Chen, Song,Chen, Yue-Gang,Gao, Pei-Sen,Liu, Dong,Ma, Hong-Xing,Mei, Tian-Sheng,Qiu, Hui,Shuai, Bin,Wang, Yun-Zhao
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p. 9872 - 9878
(2020/06/27)
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- Double-Fold Ortho and Remote C-H Bond Activation/Borylation of BINOL: A Unified Strategy for Arylation of BINOL
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A double-fold ortho and remote C-H borylation of BINOL is described. The proposed mechanisms involved electrostatically and sterically directed ortho and remote C-H activation processes, respectively. While B2eg2 (eg = ethylene glyco
- Bisht, Ranjana,Chaturvedi, Jagriti,Pandey, Gajanan,Chattopadhyay, Buddhadeb
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supporting information
p. 6476 - 6480
(2019/08/20)
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- Fast, Efficient and Low E-Factor One-Pot Palladium-Catalyzed Cross-Coupling of (Hetero)Arenes
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The homocoupling of aryl halides and the heterocoupling of aryl halides with either aryl bromides or arenes bearing an ortho-lithiation directing group are presented. The use of a Pd catalyst, in combination with t-BuLi, allows for the rapid and efficient formation of a wide range of polyaromatic compounds in a one pot procedure bypassing the need for the separate preformation of an organometallic coupling partner. These polyaromatic structures are obtained in high yields, in 10 min at room temperature, with minimal waste generation (E-factors as low as 1.5) and without the need for strict inert conditions, making this process highly efficient and practical in comparison to classical methods. As illustration, several key intermediates of widely used BINOL-derived structures are readily prepared.
- Pinxterhuis, Erik B.,Visser, Paco,Esser, Iwan,Gualtierotti, Jean-Baptiste,Feringa, Ben L.
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supporting information
p. 9452 - 9455
(2017/10/23)
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- Rapid synthesis of 3,3′ bis-arylated BINOL derivatives using a C-H borylation in situ suzuki-miyaura coupling sequence
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The increased interest in BINOL derived catalysts for asymmetric transformations has encouraged us to disclose a rapid and scalable method of preparing 3,3′ bis-arylated BINOL derivatives 1 using a one-pot CH borylation/Suzuki-Miyaura coupling sequence. T
- Ahmed, Ijaz,Clark, Daniel A.
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p. 4332 - 4335
(2014/10/16)
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- Diastereomeric resolution of rac -1,1′-bi-2-naphthol boronic acid with a chiral boron ligand and its application to simultaneous synthesis of (R)- and (S)-3,3′-disubstituted 1,1′-bi-2-naphthol derivatives
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A new concept of diastereomeric resolution has been developed where a boronic acid functionality was employed as (1) a diastereomeric resolving group with a chiral boron ligand and (2) a masked functional group for further transformation thereafter. This new diastereomeric resolution method was successfully applied to the preparation of both (R)- and (S)-3,3′- disubstituted 1,1′-bi-2-naphthol (BINOL) derivatives in a step-ecomonical manner. Racemic BINOL boronic acid reacted with a commercially available pinene-derived iminodiacetic acid as a chiral boron ligand to generate the two diastereomers in quantitative yields over a gram-scale quantity. After the removal of the chiral boron ligand from the diastereomers under mild conditions, the subsequent Suzuki coupling reaction of the resulting chiral BINOL boronic acids with aryl halides provided a series of both (R)- and (S)-BINOL derivatives in good yields. Further, both resulting diastereomers could be directly applied to the Suzuki coupling reaction without the removal of the chiral ligand.
- Lee, Chun-Young,Cheon, Cheol-Hong
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p. 7086 - 7092
(2013/08/23)
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- Pd(II)-catalyzed C-H activation/aryl-aryl coupling of phenol esters
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(Chemical Equation Presented) Although nitrogen-containing group-directed cyclopalladation reactions have been well-known, Pd(II) insertion into C-H bonds promoted by coordination of an oxygen-only group to the palladium remains rather rare. In the present study, the first cyclopalladation complex formed from a simple phenol ester was characterized by X-ray crystallography. A promising protocol for the ortho C-H activation/aryl-aryl coupling of phenol esters that was not sensitive to moisture or air was then established. The utility of the reaction was demonstrated for the synthesis of useful phenol derivatives. Copyright
- Xiao, Bin,Fu, Yao,Xu, Jun,Gong, Tian-Jun,Dai, Jian-Jun,Yi, Jun,Liu, Lei
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supporting information; experimental part
p. 468 - 469
(2010/03/25)
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- RETRACTED ARTICLE: Enantioselective organocatalytic hantzsch synthesis of polyhydroquinolines
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The four-component Hantzsch reaction provides access to pharmaceutically important dihydropyridines. To expand the utility of this method, we have developed a route under organocatalytic conditions with good yields and excellent ee's. Through catalyst scr
- Evans, Christopher G.,Gestwicki, Jason E.
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supporting information; experimental part
p. 2957 - 2959
(2009/12/05)
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- Asymmetric allylboration of aldehydes and ketones using 3,3′-disubstitutedbinaphthol-modified boronates
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Allylboronates derived from 3,3′-disubstituted 2,2′-binaphthols react with aldehydes and ketones to give the expected allylated products with up to >99:1 er. Highest selectivities were observed for aromatic ketones. The bis(trifluoromethyl) derivative is particularly outstanding in terms of reactivity, selectivity, and robustness.
- Wu, T. Robert,Shen, Lixin,Chong, J. Michael
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p. 2701 - 2704
(2007/10/03)
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