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Rapid Ti(Oi-Pr)4 facilitated synthesis of α,α,α-trisubstituted primary amines by the addition of Grignard reagents to nitriles under microwave heating conditions

✍ Scribed by Ruifang Wang; Brian T. Gregg; Wei Zhang; Kathryn C. Golden; John F. Quinn; Peng Cui; Dmytro O. Tymoshenko

Publisher
Elsevier Science
Year
2009
Tongue
French
Weight
567 KB
Volume
50
Category
Article
ISSN
0040-4039

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✦ Synopsis

A series of carbinamines (a,a,a-trisubstituted amines) have been prepared in a simple and efficient onepot procedure by the addition of Grignard reagents to a series of aliphatic, aromatic and heteroaromatic nitriles. The resulting magnesium imines are subsequently converted to the desired amine after treatment with Ti(Oi-Pr) 4 and additional microwave heating. Key to this procedure is the use of microwave heating for both steps of the reaction protocol, which significantly improves both reaction yields and reduces reaction times. In general, the Grignard addition reaction is complete within 5-10 min at 100 °C followed by conversion with Ti(Oi-Pr) 4 and additional microwave heating to give the target amines in good yields.

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Rapid, one-pot synthesis of α,α-disubsti
Rapid, one-pot synthesis of α,α-disubstituted primary amines by the addition of Grignard reagents to nitriles under microwave heating conditions
✍ Brian T. Gregg; Kathryn C. Golden; John F. Quinn; Hong-Jun Wang; Wei Zhang; Ruif 📂 Article 📅 2009 🏛 Elsevier Science 🌐 French ⚖ 488 KB

A series of a,a-disubstituted amines have been prepared in a simple and efficient one-pot procedure by the addition of Grignard reagents to a series of aliphatic, aromatic, and heteroaromatic nitriles. Key to this reported procedure is the unprecedented addition of the Grignard reagent to the nitril