Direct Synthesis of Amides by Acceptorless Dehydrogenative Coupling of Benzyl Alcohols and Ammonia Catalyzed by a Manganese Pincer Complex: Unexpected Crucial Role of Base

Amide synthesis is one of the most important transformations in chemistry and biology. The direct use of ammonia for the incorporation of nitrogen functionalities in organic molecules is an attractive and environmentally benign method. We present here a new synthesis of amides by acceptorless dehydr...

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Published inJournal of the American Chemical Society Vol. 141; no. 31; pp. 12202 - 12206
Main Authors Daw, Prosenjit, Kumar, Amit, Espinosa-Jalapa, Noel Angel, Ben-David, Yehoshoa, Milstein, David
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.08.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
SECONDARY ALCOHOLS
AMINATION
METHANOL
DIAMINES
LIBERATION
PRIMARY AMINES
LACTAMS
H-2
EFFICIENT
WATER
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Summary:Amide synthesis is one of the most important transformations in chemistry and biology. The direct use of ammonia for the incorporation of nitrogen functionalities in organic molecules is an attractive and environmentally benign method. We present here a new synthesis of amides by acceptorless dehydrogenative coupling of benzyl alcohols and ammonia. The reaction is catalyzed by a pincer complex of earth-abundant manganese in the presence of a stoichiometric base, making the overall process economical, efficient, and sustainable. Interesting mechanistic insights based on detailed experimental observations, indicating the crucial role of the base, are provided.
Bibliography:ObjectType-Article-1
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ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.9b05261