1992
DOI: 10.1021/jo00033a020
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Cobalt(II) chloride catalyzed acylation of alcohols with acetic anhydride: scope and mechanism

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Cited by 231 publications
(64 citation statements)
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“…Protection of alcohols is usually performed employing acid anhydrides or acyl chlorides in the presence of stoichiometric amounts of protonic and Lewis acids, such as p-toluenesulfonic acid, 1 scandium trifluromethanesulfonate, 2 trimethylsilyl triflouromethanesulfonate, 3 zinc chloride, 4 and cobalt chloride. 5 The above options employing acetic anhydride as acetylating agent and soluble acids as reagents or catalysts presents achieve less than 50% atom economy in the consumption of acetic anhydride by utilizing only the acetyl group. Moreover, acid halides and acid anhydrides are usually employed as the acetylating agents in the presence of an acid or base catalyst such as H2SO4, 6 PTSA, 7 Shvo's catalyst, 8 distannoxane catalyst 9 and lipase.…”
Section: Introductionmentioning
confidence: 99%
“…Protection of alcohols is usually performed employing acid anhydrides or acyl chlorides in the presence of stoichiometric amounts of protonic and Lewis acids, such as p-toluenesulfonic acid, 1 scandium trifluromethanesulfonate, 2 trimethylsilyl triflouromethanesulfonate, 3 zinc chloride, 4 and cobalt chloride. 5 The above options employing acetic anhydride as acetylating agent and soluble acids as reagents or catalysts presents achieve less than 50% atom economy in the consumption of acetic anhydride by utilizing only the acetyl group. Moreover, acid halides and acid anhydrides are usually employed as the acetylating agents in the presence of an acid or base catalyst such as H2SO4, 6 PTSA, 7 Shvo's catalyst, 8 distannoxane catalyst 9 and lipase.…”
Section: Introductionmentioning
confidence: 99%
“…Tributyl phosphine was introduced as a less basic catalyst than amines in the acetylation of alcohols [28][29]. Other metal salts such as LiClO 4 [36], CoCl 2 [37], and Mg(ClO 4 ) 2 [38] have also been successfully have been reported to show catalytic activity toward the acetylation of alcohols with acid anhydride. Number of lewis acids such as TMSCl [15][16] [22].…”
Section: Introductionmentioning
confidence: 99%
“…1 This important transformation is typically performed using acetic anhydride and/or acetyl chloride in the presence of either basic or acidic catalysts. Numerous methodologies are available for this transformation, [2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17] but most of them are homogeneous and the catalysts are non-recoverable. In addition, they have one or more disadvantages, such as prolonged reaction times, low yields, harsh conditions, use of harmful organic solvents, tedious work-up procedures, the requirement for excess reagents or catalysts and the use of explosive, moisturesensitive or expensive catalysts.…”
Section: Introductionmentioning
confidence: 99%