Sc(OTf)3 catalyzed carbon-carbon and carbon-heteroatom bond forming reactions: a review

Abstract

In recent years scandium(III) trifluoromethanesulfonate [Sc(OTf)3] has emerged as an efficient, mild, commercially available, inexpensive, water tolerant Lewis acidic catalyst in the formation of both carboncarbon and carbon-heteroatom bonds, and thereby the formation of various biologically promising organic compounds. The present review summarizes the latest developments on Sc(OTf)3-catalyzed organic transformations especially carbon-carbon and carbon-heteroatom bond forming reactions reported during the last decade.

Green Procedure for One-Pot Synthesis of Azelaic Acid Derivatives Using Metal Catalysis

“…Recently, Molybdenum and some rare earth derivatives (Sc and Yb), by their Lewis acid properties, displayed interesting activity in the oxidation of olefins [10][11][12], therefore, we planned their involvement in the oxidation of oleic acid 1 and corresponding methyl ester 1a, to replace the noneco-friendly and unrecyclable HBF 4 and H 3 PO 4 .…”

“…Results showed that selectivity improved using Scandium triflate alone, that led to the complete conversion of methyl oleate 1a into the epoxide 2a (60%) and 1,2-diol 3 (40%) without the formation of cleavage by-products (Table 1, entry 5). This indicates that Sc(OTf) 3 possessing unique Lewis acid properties is capable of activating double bond for epoxidation, or electrophilically the hydrogen peroxide, even with longer reaction times [11,12], but cannot give cleavage products.…”

One‐Pot Pseudo Five Component Synthesis of Biologically Relevant 1,2,6‐Triaryl‐4‐arylamino‐piperidine‐3‐ene‐3‐ carboxylates: A Decade Update

“…As a result, during the last decade, a good number of methods reported for the synthesis of 1,2,6‐triaryl‐4‐arylamino‐piperidine‐3‐ene‐3‐carboxylates via the one‐pot pseudo five‐component reaction of two equivalents of aldehydes, two equivalents of amines and one equivalent of β‐keto esters under various reaction conditions (Scheme ). Screening of suitable catalyst is the key to success among the other significant parameters during the synthesis of important heterocycles . For this synthesis also, along with other favorable conditions, catalyst plays a crucial role.…”

“…Screening of suitable catalyst is the key to success among the other significant parameters during the synthesis of important heterocycles. [30][31][32] For this synthesis also, along with other favorable conditions, catalyst plays a crucial role. During last decade, a variety of acidic catalysts such as metal salts, organocatalysts, solid supported heterogenous catalysts, ionic liquids, surfactants etc were employed for the synthesis of 1,2,6-triaryl-4-arylamino-piperidine-3-ene-3-carboxylates in absence or presence of various solvents at ambient or reflux conditions.…”

Lewis Acid Mediated Cyclizations: Diastereoselective Synthesis of Six- to Eight-Membered Substituted Cyclic Ethers

“…34 Recently, Sc(OTf) 3 has been employed in a variety of carbon-carbon and carbon-heteroatom bond-forming reactions. 35 A. K. Ghosh et al…”