Iodine as an Acetyl Transfer Catalyst†

Abstract

Iodine catalyses the acetylation of amines, phenols and alcohols, including tertiary ones, with acetic anhydride in excellent yield.

Mild and Highly Efficient Copper(I) Inspired Acylation of Alcohols and Polyols

“…Some notable methods include the use of I 2 [2][3][4], Br 2 [5] montmorillonite K-10 [6], FeCl 3 [7], TiCl 4 -AgClO 4 [8], LiClO 4 [9], CuSO 4 ·5H 2 O [10], TMSOTf [11], Bu 3 P in CH 2 Cl 2 [12,13], La(NO 3 ) 3 ·6H 2 O [14], HClO 4 -SiO 2 [15], molecular sieves [16], NaHCO 3 [17], Mg(NTf 2 ) 2 [18], 3-nitrobenzeneboronic acid [19], alumina [20], NBS [21], TaCl 5 [22], VO(OAc) 2 [23] and metal triflates such as Pd(PhCN) 2 (OTf) [24], Cu(OTf) 2 [25], Bi(OTf) 2 [26], In(OTf) 2 [27,28], Sc(OTf) 2 [29], Ce(OTf) 2 [30], and CoCl 2 [31,32].…”

N1,N3-Diacyl-3,4-dihydropyrimidin-2(1H)-ones: neutral acyl group transfer reagents

“…0, 130.4, 129.4, 126.6, 125.3, 123.5, 24.2, 17.7; m/z 172 (Mþ23). (12) 7,47.4,42.4,26.3,25.4,24.4,21.4;m/z 150 (Mþ23 (3H, m, ArH), 3.86 (6H, s, 2ÂOCH 3 ), 3.47-3.59 (2H, m, CH 2 NCH 3 ), 2.89 (3H, s, NCH 3 ), 2.78 (2H, t, J 7.5 Hz, CH 2 Ph), 2.05 (2H, t, J 7.8 Hz, COCH 2 CH 2 ), 1.52-1.69 (2H, m, CH 2 (CH 2 )CH 3 ), 0.87 (3H, t, J 7.5 Hz, CH 3 CH 2 ); d C (75 MHz, CDCl 3 ) 172. 9, 148.9, 147.3, 131.0, 130.7, 120.6, 111.7, 55.7, 51.6, 49.8, 35.8, 34.4, 33.3, 18.3, 13.6; m/z 266 (Mþ1).…”

“…Viscous liquid; [Found: C,66.62;H,7.43;N,8.55. C 10 H 13 NO 2 requires C,67.03;H,7.26;N,7 171.8, 147.5, 127.7, 123.3, 121.0, 119.6, 109.7, 55.6, 31.0, 9.6; m/z 202 (Mþ23). 4.3.3.…”

Highly Efficient Cationic Palladium Catalyzed Acetylation of Alcohols and Carbohydrate-Derived Polyols

“…Some notable examples include the use of tributylphosphine [6,7], bromine [8], p-Toluenesulfonic acid [9], alumina [10], scandium triflate [11], indium triflate [12,13], bismuth triflate [14], trimethylsilyl triflate [15], copper triflate [16], cerium triflate [17], ruthenium chloride [18], sulfamic acid [19], montmorillonite K-10 [20], molecular sieves [21], iron (III)chloride [22], magnesium bromide [23], tantalum chloride [24], vanadyl acetate [25], N-bromosuccinamide (NBS) [26], 3-nitrobenzeneboronic acid [27], lithium perchlorate (LiClO 4 ) [28], silica gel supported sodium hydrogen sulfate [29], sodium acetate trihydrate [1], dried sodium bicarbonate [30] and Iodine [31,32]. While these methods provides viable alternative for acetylating alcohols, some of these methods utilizes catalysts that are expensive, moisture sensitive, require long reaction times and tedious work-up protocols and sometimes result in low yields.…”