Publications (36) View all
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Article: Palladium catalyzed C-H functionalization of O-arylcarbamates: selective ortho-bromination using NBS.
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ABSTRACT: A series of cyclometalated palladium complexes derived from O-phenylcarbamates has been synthesized by the reaction of the respective carbamates with Pd(OAc)(2) in the presence of acids, CF(3)CO(2)H, CF(3)SO(3)H, and p-TsOH. The palladacycles were observed to coordinate amines and electron rich anilines but not sulfonamides or carboxamides. Analysis of the (t)Bu-NH(2) adduct of the palladacycle 2b (2b·(t)Bu-NH(2)) by NMR spectroscopy (NOE) revealed a cis-coordination of the amine. However, the amine adducts failed to undergo ortho-amination (C-N bond formation) under varied reaction conditions. Notably, the palladacycle 1d was found to react efficiently with N-iodosuccinimide (NIS) to yield the ortho-iodinated carbamate, 1e. More significantly, this reaction can be extended to a palladium-catalyzed ortho C-H bromination of aryl-O-carbamates even at 5 mol % loading of Pd(OAc)(2) using N-bromosuccinimide (NBS).The Journal of Organic Chemistry 06/2012; 77(13):5600-5. · 4.45 Impact Factor -
Article: Copper-catalyzed amidation of 2-phenylpyridine with oxygen as the terminal oxidant.
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ABSTRACT: The Cu(OAc)(2)-catalyzed, O(2)-mediated amidation of 2-phenylpyridine via C-H bond activation is reported. A variety of nitrogen reagents including sulfonamides, carboxamides, and anilines participate in the reaction in moderate to good yields.The Journal of Organic Chemistry 03/2011; 76(10):4158-62. · 4.45 Impact Factor -
Article: Copper-catalyzed Amidation of 2-phenylpyridine with O2 as the terminal oxidant
The Journal of Organic Chemistry 03/2011; 2011(10):4158. · 4.45 Impact Factor -
Article: Synthesis of Indole Derivatives with Biological Activity by Reactions Between Unsaturated Hydrocarbons and N-Aromatic Precursors
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ABSTRACT: The present review is devoted to illustrate the state of the art of the syntheses of indoles, focusing particularly on the most recent developments of new synthetic approaches. Emphasis is given to the preparation of natural products or bioactive compounds containing the indole unit. We present a historical perspective of indole synthesis showing the strategies by choosing the nitrogen precursors. The review is organized sharing the indole synthetic approaches by using different nitrogen-containing functional groups in aromatic substrates used as source of the nitrogen of the indole moiety. Some functional groups and some typical reactions are particularly stressed and highlighted because of the limited coverage given in previous reviews published on this topic. Other synthetic approaches more used and discussed in recent, complete and excellent reviews on the topic are summarized but the most recent published results are highlighted. Our interest is particularly focused on the indolization procedures and on the different methods used for the ring closure and no attention is given to modification of indole structures starting from molecules with a preformed indole unit. Intriguing indole syntheses are continually discovered and the importance that the scientific community gives to these new developments is connected with the strategic role of molecules containing the indole unit. Indoles are the class of heterocycles with more applications and extensive interest due to their biological and pharmacological activity.Current Organic Chemistry 11/2010; 14(20):2409-2441. · 3.06 Impact Factor -
Article: Iodine-Catalyzed Aminosulfonation of Hydrocarbons by Imidoiodinanes. a Synthetic and Mechanistic Investigation.
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ABSTRACT: The amino-functionalization of a range of benzylic and some aliphatic saturated and unsaturated hydrocarbons by reaction with imido-iodinanes (PhI═NSO(2)Ar) is catalyzed by I(2) under operationally simple and mild conditions. The first examples of 1,2-functionalization of unactivated C-H bonds using imido-iodinanes as aminating agents are reported. Mechanistic investigations, including Hammett analysis, kinetic isotope effects, a cyclopropane clock experiment, and stereoselectivity tests, are indicative of a stepwise pathway in C-N bond formation. Investigation into the nature of the active aminating species has led to the isolation of a novel aminating agent formulated as (ArSO(2)N)(x)I(y) (x = 1, y = 2; or x = 3, y = 4).The Journal of Organic Chemistry 10/2010; · 4.45 Impact Factor
