By Lixiong Shao, Jianmei Lu, Min Shi
Modern natural synthesis has paid a lot cognizance to the chemistry of small carbocycles. Vinylidenecyclopropanes (VDCPs), that have strained cyclopropyl team hooked up with an allene moiety and but are thermally strong and reactive components in natural chemistry, are flexible intermediates in natural synthesis. during this quantity, Dr. Lixiong Shao, Dr. Jianmei Lu and Prof. Dr. Min Shi assessment their investigations at the chemistry of VDCPs, ordinarily together with the education, the reactivities upon remedy with Lewis or Brønsted acid, in addition to transition steel catalysts and a few different miscellaneous analogues. The contributions aroused a renaissance of cationic intermediates within the chemistry of VDCPs.
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Additional resources for Chemical Transformations of Vinylidenecyclopropanes
Example text
8 Lewis Acid-Mediated Reactions of VDCPs with Alcohols or Ethers Ph OH Nd(OTf) Ph Ph 3 n+ Ph -OH Ph Ph 136 132a (n = 1) 133a (n = 2) Ph Ph + Ph . 38 Plausible mechanism for the Nb(OTf)3-catalyzed reactions of VDCP 1b with enol 132a and dienol 133a intermediate 148, which affords intermediate 149 via the intramolecular Friedel– Crafts reaction with the adjacent aromatic R3 group. 40). 41. Similarly, intermediates 146a, 150 and 151 will be formed in the Lewis acid-catalyzed reactions of 141a with VDCPs 1.
Angew Chem Int Ed 45:3314–3317 Chapter 3 Transition Metal-Catalyzed Transformations of VDCPs Abstract Transition metals such as palladium and rhodium-catalyzed transformations of vinylidenecyclopropanes are introduced in this chapter. Á Á Á Keywords Vinylidenecyclopropanes Transition metal Palladium Rhodium Coupling reaction Á In 2006, Shi et al. 1) [1–4]. In 2009, Shi and co-workers reported the palladium-catalyzed coupling reactions of VDCPs 1 with 2-iodophenols 168 and N-(2-iodophenyl)-4-methylbenzenesulfonamide 170.
2) [3]. 3. Initially, the fluoric cation F+ and the anionic intermediate (PhSO2)2N- are generated from NFSI under the stardard reaction conditions [4–6]. Then the fluoric cation F+ adds to the C10 position of VDCPs 1 to give cationic intermediate 186. Intermediate 186 can give the cyclopropyl ring-opened cationic intermediate 187, which can be transformed to the final products 185 via deprotonation. 4) [1, 7]. In the following research, it was observed that the reactions of VDCPs 1 with equimolar amount of bromine or iodine at low temperature can produce the corresponding addition products 190–192, depending on the nature of VDCPs, in moderate to good yields at -40 and -100 °C, respectively.