Facile Deprotection of Bulky (Trialkylsilyl)acetylenes with Silver Fluoride

Kim, Sanghee; Kim, Bogyeong; In, Jinkyung

doi:10.1055/s-0029-1216788

Cited by 29 publications

(24 citation statements)

References 2 publications

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“…Further treatment of 16 with TBAF afforded 17a in 90% yield with retention of the TMS group, and the structure was confirmed by X-ray crystallographic analysis. However, when 16 was reacted with AgF, 22 dienone 17 was obtained in 85% yield with removal of its both silyl groups. hydrogenation.…”

Section: Scheme 1: Retrosynthetic Analysis Of Propindilactone Gmentioning

confidence: 99%

Asymmetric Total Synthesis of Propindilactone G

et al. 2015

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A concise total synthesis of (+)-propindilactone G, a nortriterpenoid isolated from the stems of Schisandra propinqua var. propinqua, has been achieved for the first time. The key steps of the synthesis include an asymmetric Diels-Alder reaction, a Pauson-Khand reaction, a Pd-catalyzed reductive hydrogenolysis reaction, and an oxidative heterocoupling reaction. These reactions enabled the synthesis of (+)-propindilactone G in only 20 steps. As a consequence of our synthetic studies, the structure of (+)-propindilactone G has been revised.

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Section: Scheme 1: Retrosynthetic Analysis Of Propindilactone Gmentioning

confidence: 99%

Asymmetric Total Synthesis of Propindilactone G

et al. 2015

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“…Likewise, aroyl chlorides successfully underwent Sonogashira coupling and desilylation steps to give terminally unsubstituted ynones that were subsequently transformed to 1-substituted-4-phenylacyl-1H-1,2,3-triazoles 16 under dielectric heating (Scheme 9) [70]. In a related study, the one-pot synthesis of 1-substituted 4-acyl-triazoles 17 was improved by (1) switching to the more robust TIPS (tris(isopropyl)silyl) protecting group; (2) reducing the amount of triethylamine in the Sonogashira step to one stoichiometrically necessary equivalent, as previously shown for TMS-alkynone formation by Karpov and Müller [79]; and (3) employing AgF as an efficient reagent for the removal of the TIPS group [80]. In addition, the reaction proceeds smoothly at room temperature and gives rise to good yields (Scheme 10) [81].…”

Section: Methodsmentioning

confidence: 99%

Sequentially Palladium-Catalyzed Processes in One-Pot Syntheses of Heterocycles

Lessing

Müller

2015

Applied Sciences

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Sequentially Pd-catalyzed processes are excellent entries to heterocycle synthesis. The broad mechanistic variety combined with often very mild reaction conditions allow the concatenation of elementary organic and organometallic steps to novel sequences in the sense of one-pot domino and multicomponent reactions. Given the numerous opportunities of alkyne coordination and their Pd-mediated transformations, alkynylation and carbometallation play a key role, both for purely organometallic sequences as well as in those processes that are intercepted by cyclocondensation. Pd-catalyzed aminations also find more and more entry into novel heterocycle syntheses based upon this theme.

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“…Commercial TBAF is sold as a solution (1 M ) in THF containing water (wt.‐5 %), which is usually sufficient. Deprotection by use of AgF offers an alternative to TBAF, and in the presence of a bromine source it can be used to insert a halogen en route to the formation of buta‐1,3‐diyenes 93…”

Section: Acetylene Protecting Groupsmentioning

confidence: 99%