Aug 06, 2014 · Over the past four decades, significant advances have been made in the development of traceless activation groups (TAGs) such as cuprates, boronic acids, halides, and Grignard reagents that enable a broad range of organic structures to participate as nucleophiles or donor components in this 1,4-coupling pathway. 2,3 Expanding upon this theme, we recently questioned whether simple and abundant carboxylic acids might be generically 5 employed as a traceless activation group for radical 1,4
The cyano group was used as a traceless activation group for the [3+2] cycloaddition of azomethine ylides in a two-step process, thereby providing a highly effective approach to 5-unsubstituted Sep 26, 2018 · Complex tertiary alkylamines are prepared in one step from readily available amines, carbonyls and alkenes, via the visible-light-mediated reduction of in-situ-generated iminium ions to form alkyl The direct application of carboxylic acids as a traceless activation group for radical Michael additions has been accomplished via visible light-mediated photoredox catalysis. Photon-induced Jun 01, 2004 · Designing a new anchoring group can be essential for synthesis success, especially for small molecules on solid supports. Many novel linkers have recently been developed. Traceless linkers can be excised efficiently and quantitatively when desired while leaving behind no trace of the solid-phase synthesis. Additional to water as H-bond donor present in our solvent mixture, we evaluated different activation modes for the LUMO lowering of carbonyl group, 22 including Schreiner's thiourea, 23 as well as different lanthanide-based, water-compatible Lewis acids. 24,25 Interestingly, the choice of the activation mode (entries 2 and 3), as well as the The direct application of carboxylic acids as a traceless activation group for radical Michael additions has been accomplished via visible light-mediated photoredox catalysis. Photon-induced The direct application of carboxylic acids as a traceless activation group for radical Michael additions has been accomplished via visible light-mediated photoredox catalysis. Photon-induced
Carboxylic acids as a traceless activation group for conjugate additions: a three-step synthesis of (±)-pregabalin L Chu, C Ohta, Z Zuo, DWC MacMillan Journal of the American Chemical Society 136 (31), 10886-10889 , 2014
The direct application of carboxylic acids as a traceless activation group for radical Michael additions has been accomplished via visible light-mediated photoredox catalysis. Photon-induced Jan 01, 2015 · Carboxylic acids as a traceless activation group for conjugate additions: a three-step synthesis of (±)-pregabalin. Aug 6, 2014 · Journal of the American Chemical Society 14.70 # 1 Lingling Chu H-Index: 21 The direct application of carboxylic acids as a traceless activation group for radical Michael additions has been accomplished via visible light-mediated photoredox catalysis. Photon-induced The cyano group was used as a traceless activation group for the [3+2] cycloaddition of azomethine ylides in a two-step process, thereby providing a highly effective approach to 5-unsubstituted pyrrolidines.
traceless activation group that would (i) allow ð-neutral or ð-deficient substrates to function as suitable nucleophiles for iminium catalysis, while (ii) enabling site-specific alkylation of aromatic nucleophiles outside of the constraints of Friedel-Crafts regioselectivity. Herein we report the first use of vinyl and
Mar 09, 2020 · We reasoned appending a vinyl group to the carbene C., Zuo, Z. & MacMillan, D. W. C. Carboxylic acids as a traceless activation group for conjugate additions: a three-step synthesis of A new neutral silicon-based traceless activation group (TAG) for visible-light photoredox-catalyzed hydroalkoxymethylation of alkenes is presented. This reaction involves in-situ-generated alkoxymethyl radical via single electron oxidation (SET) of α-TMS-substituted ethers, followed by subsequent conjugate addition to activated alkenes. Dec 18, 2014 · Chu L, Ohta C, Zuo Z, MacMillan DWC. Carboxylic acids as a traceless activation group for conjugate additions: a three-step synthesis of (±)-pregabalin. J. Am. Chem. Soc. 2014; 136:10886–10889. [PMC free article] Dec 17, 2014 · Highly substituted carbon–carbon bonds are constructed using a simple iron catalyst and an inexpensive silane: more than 60 examples of this reaction — in which heteroatom-substituted olefins Nov 12, 2013 · Ritika Sharma, Rakesh Kumar, Inder Kumar, Upendra Sharma, RhIII‐Catalyzed Dehydrogenative Coupling of Quinoline N‐Oxides with Alkenes: N‐Oxide as Traceless Directing Group for Remote C–H Activation, European Journal of Organic Chemistry, 10.1002/ejoc.201501246, 2015, 34, (7519-7528), (2015). Jundong Li, Huaibo Zhao, Xunjin Jiang, Xiance Wang, Haiming Hu, Lei Yu, Yandong Zhang, The Cyano Group as a Traceless Activation Group for the Intermolecular [3+2] Cycloaddition of Azomethine Ylides: A Five‐Step Synthesis of (±)‐Isoretronecanol, Angewandte Chemie International Edition, 10.1002/anie.201500961, 54, 21, (6306-6310), (2015). In an effort to dramatically increase the scope of organocatalytic Friedel–Crafts alkylations, we recently disclosed the utility of vinyl and heteroaryl trifluoroborate salts. 37 As detailed in Scheme 2, the introduction of trifluoroborate as a traceless activation group has enabled an expanded range of electron-rich and electron-neutral π-nucleophiles to participate in iminium-catalyzed Friedel–Crafts additions while overcoming the regioselectivity limitations that are inherent to