Journal ArticleDOI
Substitution of alcohols by N-nucleophiles via transition metal-catalyzed dehydrogenation
Qin Yang,Qingfu Wang,Zhengkun Yu +2 more
TLDR
This critical review summarizes the recent advances in "BH" substitution of alcohols by N-nucleophiles since 2009 and provides new principles for establishing green processes to replace the relevant traditional synthetic methods for C-N bond formation.Abstract:
Transition metal-catalyzed substitution of alcohols by N-nucleophiles (or N-alkylation of amines and related compounds with alcohols) avoids the use of alkylating agents by means of borrowing hydrogen (BH) activation of the alcohol substrates. Water is produced as the only by-product, which makes the “BH” processes atom-economic and environmentally benign. Diverse types of homogeneous organometallic and heterogeneous transition metal catalysts, and substrates such as N-nucleophiles including amines, amides, sulfonamides and ammonia, and various alcohols, can be used for this purpose, demonstrating the promising potential of “BH” processes to replace the procedures using traditional alkylating agents in pharmaceutical and chemical industries. Borrowing hydrogen activation of alcohols for C–N bond formation has recently been paid more and more attention, and a lot of new and novel procedures and examples have been documented. This critical review summarizes the recent advances in “BH” substitution of alcohols by N-nucleophiles since 2009. “Semi-BH” N-alkylation processes with or without an external hydrogen acceptor are also briefly presented. Suitable discussion of the “BH” strategy provides new principles for establishing green processes to replace the relevant traditional synthetic methods for C–N bond formation.read more
Citations
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Journal ArticleDOI
Advances in One-Pot Synthesis through Borrowing Hydrogen Catalysis
TL;DR: The objective of the present review is to give a global overview on the topic starting from those contributions published prior to the emergence of the BH concept to the most recent and current research under the term of BH catalysis.
Journal ArticleDOI
Transition-Metal-Catalyzed Cleavage of C-N Single Bonds.
TL;DR: This paper presents the results of aalysis experiments conducted at the BNLMS and Nankai University with real-time measurements of the response of the H2O-O2/O2 mixture to E2O/O3 mixture.
Journal ArticleDOI
Efficient and selective N-alkylation of amines with alcohols catalysed by manganese pincer complexes.
Saravanakumar Elangovan,Jacob Neumann,Jean-Baptiste Sortais,Kathrin Junge,Christophe Darcel,Matthias Beller +5 more
TL;DR: It is shown that the selective N-alkylation of amines with alcohols can be catalysed by defined PNP manganese pincer complexes and the chemoselective monomethylations of primary amines using methanol under mild conditions are reported.
Journal ArticleDOI
Recent Advances in Aerobic Oxidation of Alcohols and Amines to Imines
Bo Chen,Lianyue Wang,Shuang Gao +2 more
TL;DR: In this article, the authors focused on three new approaches, namely, the cross-coupling of alcohols with amines, the self coupling of primary amines and the oxidative dehydrogenation of secondary amines.
Journal ArticleDOI
C-Alkylation of Ketones and Related Compounds by Alcohols: Transition-Metal-Catalyzed Dehydrogenation.
TL;DR: This Minireview summarizes the advances during the last five years in transition-metal-catalyzed BH α-alkylation of ketones, and β-alkYLation of secondary alcohols with alcohols.
References
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Journal ArticleDOI
Catalytic dehydrogenative cross-coupling: forming carbon-carbon bonds by oxidizing two carbon-hydrogen bonds
Charles S. Yeung,Vy M. Dong +1 more
Journal ArticleDOI
Dehydrogenation as a substrate-activating strategy in homogeneous transition-metal catalysis.
Journal ArticleDOI
Applications of acceptorless dehydrogenation and related transformations in chemical synthesis.
TL;DR: Acceptorless dehydrogenation and related dehydrogenative coupling reactions have the potential for redirecting synthetic strategies to the use of sustainable resources, devoid of toxic reagents and deleterious side reactions, with no waste generation.
Journal ArticleDOI
Hydrogen autotransfer in the N-alkylation of amines and related compounds using alcohols and amines as electrophiles.
Journal ArticleDOI
Borrowing hydrogen in the activation of alcohols
TL;DR: In this paper, the metal catalyst returned the hydrogen to the transformed carbonyl compound, leading to an overall process in which alcohols can be converted into amines, compounds containing CC bonds and β-functionalised alcohols.