Joseph Teng TA: Sergey Literature Assignment 1.

To synthesize 2a, I would use phenylethyl ketone and add CuBr2, chloroform, and ethyl acetate. 2. Mech:

3. 4.

5. 6.

7.

The role of indium is that its a readily available Lewis Acid and its very stabile to both water and air. It enables allylation of aldehydes as well as aldol and Mannich reactions. Transition metal-catalyzed syntheses of furans suffer from moderate yields for Pd(II) and Pt(II) and also has a limited substrate scope for Au(III) and Mo(V). Some Lewis acid-mediated syntheses of furans exhibit poor functional group tolerance. And so it was desirable to discover an efficient methodology that employed mild and atom-economical reaction conditions. Furans are useful compounds to synthesize because they have many very versatile applications in organic synthesis and appear in many natural products. The alcohol formed in equation 1 doesnt further reacto to form an epoxide because the required backside displacement of the Br by the neighboring alkoxide couldnt occur, as the nucleophilic attack from the less hindered side of the ketone produces the unreactive synhydroxybromide. Fukuda, Y.; Shiragami, H.; Utimoto, K.; Nozaki, H. J. Org. Chem. 1991, 56, 5816 5819 One of the articles that the authors referenced was named Synthesis of Substituted Furans by Palladium-Catalyzed Cyclization of Acetylic Ketones. In this article, the authors synthesized furans using palladium as the catalyst via intramolecular oxypalladation-protodepalladation giving 2,5-disubstituted furans or oxypalladation-carbodepalladation with allyl halides affording 2,3,5-trisubstituted furans. However, when Palladium is used as the metal for a transition metalcatalyzed synthesis of a furan, yield is not very high when in the presence of water. The current article based a lot of information of this article, as both articles are dealing with the synthesis of furans via transition metal-catalyzed reactions and Lewis acid-mediated syntheses. And so, based off the information that Pd(II) was not the best transition metal, the current authors decided to exploit the properties of Indium and test it as a catalyst to create 2,3,5-Trisubstituted Furans.