Direct access toN-alkylated amines and iminesviaacceptorless dehydrogenative coupling catalyzed by a cobalt(ii)-NNN pincer complex

A Co(ii)-NNN pincer complex catalyzed directN-alkylation of anilines with alcoholsviahydrogen auto-transfer and selective acceptorless dehydrogenative coupling of benzylamines with alcohols affording imines with the liberation of molecular hydrogen and water is reported.

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Direct Synthesis of Amides by Dehydrogenative Coupling of Amines with either Alcohols or Esters: Manganese Pincer Complex as Catalyst

Angewandte Chemie International Edition ◽

10.1002/anie.201709180 ◽

2017 ◽

Vol 56 (47) ◽

pp. 14992-14996 ◽

Cited By ~ 84

Author(s):

Amit Kumar ◽

Noel Angel Espinosa-Jalapa ◽

Gregory Leitus ◽

Yael Diskin-Posner ◽

Liat Avram ◽

...

Keyword(s):

Direct Synthesis ◽

Dehydrogenative Coupling ◽

Pincer Complex

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Sustainable Synthesis of Quinazoline and 2-Aminoquinoline via Dehydrogenative Coupling of 2-Aminobenzyl Alcohol and Nitrile Catalyzed by Phosphine-Free Manganese Pincer Complex

Organic Letters ◽

10.1021/acs.orglett.9b00939 ◽

2019 ◽

Vol 21 (9) ◽

pp. 3223-3227 ◽

Cited By ~ 18

Author(s):

Kalicharan Das ◽

Avijit Mondal ◽

Debjyoti Pal ◽

Dipankar Srimani

Keyword(s):

Dehydrogenative Coupling ◽

Pincer Complex

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Copper-Catalyzed Cross Dehydrogenative Coupling ofN,N-Disubstituted Formamides and Phenols: A Direct Access to Carbamates

Advanced Synthesis & Catalysis ◽

10.1002/adsc.201400659 ◽

2015 ◽

Vol 357 (2-3) ◽

pp. 515-522 ◽

Cited By ~ 25

Author(s):

Wajid Ali ◽

Saroj K. Rout ◽

Srimanta Guin ◽

Anju Modi ◽

Arghya Banerjee ◽

...

Keyword(s):

Direct Access ◽

Dehydrogenative Coupling

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ChemInform Abstract: Copper-Catalyzed Cross Dehydrogenative Coupling of N,N-Disubstituted Formamides and Phenols: A Direct Access to Carbamates.

ChemInform ◽

10.1002/chin.201525113 ◽

2015 ◽

Vol 46 (25) ◽

pp. no-no

Author(s):

Wajid Ali ◽

Saroj K. Rout ◽

Srimanta Guin ◽

Anju Modi ◽

Arghya Banerjee ◽

...

Keyword(s):

Direct Access ◽

Dehydrogenative Coupling

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Manganese Catalysed Dehydrogenative Synthesis of Urea Derivatives and Polyureas

10.26434/chemrxiv-2021-m2hvl ◽

2021 ◽

Author(s):

Aniekan Owen ◽

Annika Preiss ◽

Angus McLuskie ◽

Chang Gao ◽

Gavin Peters ◽

...

Keyword(s):

Pharmaceutical Drugs ◽

Urea Derivatives ◽

Coupling Process ◽

Dehydrogenative Coupling ◽

Pincer Complex ◽

Reaction Proceeds ◽

Earth Abundant ◽

Broad Variety ◽

Resin Precursors ◽

A Current

Urea derivatives are prevalent intermediates in the synthesis of resin precursors, dyes, agrochemicals, and pharmaceutical drugs. Furthermore, polyureas are useful plastics with applications in coating, adhesive, and biomedical industries and have a current annual market of USD 885 million. However, the conventional methods for the synthesis of urea derivatives and polyureas involve toxic reagents such as (di)isocyanates, phosgene, CO, and azides. We present here the synthesis of (poly)ureas using much less toxic reagents - (di)amines, and methanol via a catalytic dehydrogenative coupling process. The reaction is catalyzed by a pincer complex of an earth-abundant metal, manganese, and liberates H2 gas, valuable by itself, as the only by-product making the overall process atom-economic, and sustainable. A broad variety of symmetrical, and unsymmetrical urea derivatives and polyureas have been synthesized in moderate to quantitative yields using this catalytic protocol. Mechanistic insights have also been provided using experiments and DFT computation suggesting that the reaction proceeds via an isocyanate intermediate.

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