A Simple Chemoselective Method for the Deprotection of Acetals and Ketals Using Bismuth Nitrate Pentahydrate

Eash, Kyle J.; Pulia, Michael S.; Wieland, Laura C.; Mohan, Ram S.

doi:10.1021/jo001202g

Cited by 53 publications

(19 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In acetonitrile/water, C-O bond fission is considered to occur preferentially via hydrolysis under the catalysis of nitric acid generated by hydrolysis of Bi(NO 3 ) 3´5 H 2 O, [15] while the C-S bond may be cleaved in wet benzene via oxidation under the catalysis of NO + generated by decomposition of Bi(NO 3 ) 3´5 H 2 O, which will be discussed below. The recent report on a similar deprotection of O,O-acetals describes that a suspension of Bi(-NO 3 ) 3´5 H 2 O in water is acidic and that the resulting nitric acid promotes the deprotection.…”

Section: Deprotection Of So-and Oo-acetalscontrasting

confidence: 90%

“…[5a,14] On the other hand, a simple chemoselective method for the deprotection of O,O-acetals has been developed using Bi(NO 3 ) 3´5 H 2 O as a catalyst quite recently. [15] The results of the deprotection of S,O-and O,Oacetals are summarized in Table 4. Acetonitrile/water (4/1 v/v) was found to be a complementary solvent to the wet benzene used for the deprotection of S,S-acetals; much better yields were obtained in acetonitrile/ water (runs 8, 12 and 13) than in wet benzene (runs 7, 11 and 14), while the opposite trends were observed in runs 3-4 and 9-10.…”

Section: Deprotection Of So-and Oo-acetalsmentioning

confidence: 99%

See 1 more Smart Citation

A Catalytic Deprotection ofS,S-,S,O- andO,O-Acetals Using Bi(NO3)3⋅5 H2O under Air

et al. 2001

View full text Add to dashboard Cite

S,S‐Acetals are smoothly deprotected with air in the presence of a catalytic amount of Bi(NO3)3⋅5 H2O (1–50 mol %) under ambient conditions to regenerate the original carbonyl compounds in good to excellent yield. This mild, simple, and environmentally benign system is successfully applied to the deprotection of S,O‐ and O,O‐acetals and is compatible with various functional groups. From the mechanistic study of the reaction, the catalytic cycle is considered to be composed of the following four steps: (1) the nitrososulfonium ion of the S,S‐acetal is formed by attack of nitrosonium ion (NO +) generated from Bi(NO3)3⋅5 H2O through the equilibrium with NO2, (2) the nitrososulfonium ion is hydrolyzed to afford the hemithioacetal and thionitrite, (3) the hemithioacetal collapses to the original carbonyl compound and thiol, which is oxidized by NO + to give disulfide and NO via thionitrite, and (4) the NO captures molecular oxygen from air to regenerate NO2.

show abstract

Section: Deprotection Of So-and Oo-acetalscontrasting

confidence: 90%

Section: Deprotection Of So-and Oo-acetalsmentioning

confidence: 99%

A Catalytic Deprotection ofS,S-,S,O- andO,O-Acetals Using Bi(NO3)3⋅5 H2O under Air

et al. 2001

View full text Add to dashboard Cite

show abstract

“…Bismuth nitrate pentahydrate (BNP) possesses the optimum blend of all the above-said properties. The potential of BNP as a versatile and efficient catalyst for several reactions has already been explored [42][43][44][45][46][47][48]. Encouraged by the results obtained with BNP as a catalyst for Ferrier rearrangement, we planned a systematic study in which all the intricacies of the BNP-mediated reactions were probed.…”

Section: Screening Of Metal Nitratesmentioning

confidence: 99%

Metal nitrates catalysed O-glucosylation using acetyl glucal in organic solvents and ionic liquids: A comparative investigation

Naik

Nara

Harjani

et al. 2005

Journal of Molecular Catalysis A: Chemical

View full text Add to dashboard Cite

“…Recently, bismuth nitrate has emerged as an efficient Lewis acid [14][15][16] due to its relatively low toxicity, readily availability at a low cost and tolerance to trace amounts of water. Hence, we considered BiNO 3 ·5H 2 O to be an ideal Lewis acid to address some of the limitations posed by known methods.…”

mentioning

confidence: 99%

An Efficient One-Pot Synthesis of α-Amino Phosphonates Catalyzed by Bismuth Nitrate Pentahydrate

Bhattacharya¹,

Kaur²

2007

Synlett

View full text Add to dashboard Cite

A simple, efficient, and environmentally benign method has been developed for the synthesis of a-amino phosphonates through a one-pot reaction of aldehydes with amines and diethyl phosphite in the presence of bismuth nitrate pentahydrate as a catalyst. Some of the major advantages of this protocol are: good yields, the involvement of a less-expensive and non-toxic catalyst, mild and solvent-free reaction conditions and also tolerance towards other functional groups present in the substrates. Eighteen examples are described, highlighting the substrate scope of the reaction.

show abstract

A Simple Chemoselective Method for the Deprotection of Acetals and Ketals Using Bismuth Nitrate Pentahydrate

Cited by 53 publications

References 20 publications

A Catalytic Deprotection ofS,S-,S,O- andO,O-Acetals Using Bi(NO3)3⋅5 H2O under Air

A Catalytic Deprotection ofS,S-,S,O- andO,O-Acetals Using Bi(NO3)3⋅5 H2O under Air

Metal nitrates catalysed O-glucosylation using acetyl glucal in organic solvents and ionic liquids: A comparative investigation

An Efficient One-Pot Synthesis of α-Amino Phosphonates Catalyzed by Bismuth Nitrate Pentahydrate

Contact Info

Product

Resources

About