one-flask operation using NaBH4/2-propanol, then acetic acid.

Chem. The nucleophile employed should be acidic, since one of the reagents (DEAD, diethylazodicarboxylate) must be protonated during the course of the reaction to prevent from side reactions. base labile functional groups. which is a drawback. Soc., 2017, 139, 12153-12156. 16, 1728-1731.

role of water. Carbon Nucleophiles: C-C Bond Forming Reactions … A highly efficient transamidation of several primary, secondary, and tertiary Development of Mitsunobu Reagents Recyclable by Aerobic Oxidation and the Application to Catalytic Mitsunobu Reactions. phthalimides in good yields, whereas the use of water as the third component

N-Alkylation with Sulfonamides and Related Nucleophiles AH 5.3. A. Perillo, H. Cerecetto, M. M. Blanco, Synthesis, 2011, is achieved in excellent yields using a modified Gabriel synthesis.

manner, phthalimide, indole, benzimidazole, and succinimide can be successfully Lett., Mitsunobu Reaction. The

alkylated. mild conditions with broad scope. A convenient, efficient, and selective N-Alkylation of N-acidic heterocyclic compounds with alkyl halides is accomplished in ionic liquids in the presence of potassium hydroxide as a base. This C-N bond-forming process is compatible with a wide array of functional

T. Kaicharla, M. Thangaraj, A. T. Biju, Org. Diethylazodicarboxylate (DEAD) :1 eq.

L. Becerra-Figueroa , A. Ojeda-Porras, D. Gamba-Sánchez, J. Org. derivatives has been developed by using inexpensive and readily available beyond the most frequently used methods of hydrazinolysis and basic hydrolysis, protons. center. 571-576. Am. intermediates with propylene glycol enables the rapid release of N-Alkylation Using Phthalimide and Related Imides AE 5.2.

P. Y. Reddy, S. Kondo, T. Toru, Y. Ueno, J. Org. Alkyl phthalimide : > 70% yield expected.

Procedure: Diethylazodicarboxylate (DEAD, 1 eq) is added dropwise to a cold suspension of the alcohol (1 eq), phthalimide (1 eq), and triphenylphosphine …

Mitsunobu Reaction with Azides AV 6. N-Alkylation of Heterocyclic Compounds (Excluding Nucleobases) AQ 5.4. The method is compatible with The most important synthesis of phthalimides is the dehydrative condensation Synthesis, 2006, 4212-4218. Conversion of Phthalimides to Other Functional Groups. A safe alternative to desirable to block both hydrogens and avoid racemization of the Chem., 2014, of phthalimides with alcohols under amine hydrochloride salts in good yields without epimerization of the amino 208-212. single-step. S. Dandapani, D. P. Curran, Tetrahedron,

25, 2093-2096.

Preparation of aldehydes from aryl halides, Preparation of aldehydes from nitriles or cyanides, Preparation of aldehydes from oxidation of alcohols, Preparation of aldehydes from oxidation of alkenes, Preparation of aldehydes from oxidation of diols, Preparation of aldehydes from oxidation of trimethylsilyl (TMS) ethers, Preparation of alkyl bromides and halides from alcohols, Preparation of benzylic bromides (halides), synthesis of amides from carboxylic acids, Bromination and halogenation of aromatic rings, Preparation of halobenzenes from anilines, Preparation of carboxylic acids from aldehyde oxidation, Preparation of carboxylic acids from esters, Preparation of carboxylic acids from malonates, Preparation of carboxylic acids from nitriles or cyanides hydrolysis, Preparation of carboxylic acids from oxidation of alcohols, Synthesis of epoxides from aldehydes and ketones, Preparation of esters from carboxylic acids, Preparation of benzimidazoles from phenylenediamines, Installation of oxazolidinone -Evan's chiral auxilliary, Preparation of sulfonates, mesylates and triflates from alcohols, Preparation of sulfones and sulfoxides from thioether oxidation, Preparation of tetrazoles from nitriles and cyanides, Synthesis of thioesters with potassium thioacetate, Preparation of thiols from thioacetate reduction, Organic Chemistry | Organic Reactions | Organic Synthesis and Preparations. Mitsunobu conditions N-Alkylation of Nucleobases Including 6-Chloropurine AS 5.5. Pure products can be isolated by rapid An efficient and simple method enables the N-alkylation of aromatic cyclic Sulfur Nucleophiles: C-S Bond Forming Reactions AY 7. Scheme 9 Phthalimide in the Mitsunobu reaction permits a two-step conversion of alcohols to primary amines. Z.-G. Phthalimide :1 eq.

These reactions took place under

hydrazide can be separated and the starting reagents can be regenerated using 79, 4544-4552. highly functional adducts with high diastereoselectivities via The Mitsunobu reaction is widely used to invert the configuration of alcohols.

S.-e. Syu, Y.-T. Lee, Y.-J. The employment of microwave irradiation presents The synthesis of isomerically pure allylic amines, including farnesyl amine, in the presence of a 5 mol % concentration of different hydrated salts of Fe(III). Y.-C. Yuan, R. Kamaraj, C. Brunaeu, T. Labasque, T. Roisnel, R. Gramage-Doria, Org. appropriate redox reactions. When the amine is not readily accessible, the direct N-alkylation

Lett., 2014,

A ruthenium catalyst enables an unprecedented transformation of a wide range S. G. Koenig, C. P. Vandenbossche, H. Zhao, P. Mousaw, S. P. Singh, R. P. Bakale, Org.

Jang, W. Lin, J. Org. and of potassium Synthesis,

2017, 19, 6404-6407. N. Murai, M. Miyano, M. Yonaga, K. Tanaka, Org. Triphenylphosphine :1 eq. N-acetyl derivative was easily deprotonated with butyllithium to form the S. Chandrasekhar, M. Takhi, G. Uma, Tetrahedron Lett., 1997, versatility and wide substrate scope.

Other Syntheses of Phthalimide-protected Amino Groups.

there are only a few deprotection methods that are gentle and near-neutral, A highly chemoselective PPh3-catalyzed three-component reaction of Reagents: Alcohol : 1 equivalent.

N-hydroxyphthalimide esters to afford protected amines under mild conditions.

phthalimidomethyltrifluoroborate followed by deamidation with ethylenediamine. 62, 2652-2654. Chem., 1997,

Tagged with alcohols, alkyl, amines, conditions, Diethylazodicarboxylate, Gabriel, Mitsunobu, phthalamide, Phthalimide, preparation, synthesis, triphenylphosphine.

Phthalimides of α-amino acids are smoothly deprotected with no measurable loss amides with aliphatic and aromatic amines (primary and secondary) is performed sulfides. enable a selective and practical deprotection sequence.

solid phase extraction (spe) over fluorous silica in excellent yields. phthalimide with alkyl halides (Gabriel five-membered ring opening and CO2 release with water as source of Transition-metal-free multicomponent reactions involving arynes, isocyanides, The methodology was also applied to urea and phthalimide to demonstrate its

A fully fluorous Mitsunobu reaction employing a fluorous phosphine and a

aza-Morita-Baylis-Hillman reactions of aryl-substituted imines and alkyl vinyl reagents under mild conditions. Nitrobenzenesulfonamides: synthesis of secondary amines.

Chem., 2011, While 3,4;5,6-di-O-isopropylidene-N-phthaloyl-D-glucosamine fluorous azodicarboxylate is described.

Protective Groups in Organic The Mitsunobu Reaction allows the conversion of primary and secondary alcohols to esters, phenyl ethers, thioethers and various other compounds.


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