- Intramolecular C?H Amination of N-Alkylsulfamides by tert-Butyl Hypoiodite or N-Iodosuccinimide
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1,3-Diamines are an important class of compounds that are broadly found in natural products and are also widely used as building blocks in organic synthesis. Although the intramolecular C?H amination of N-alkylsulfamide derivatives is a reliable method for the construction of 1,3-diamine structures, the majority of these methods involve the use of a transition-metal catalyst. We herein report on a new transition-metal-free method using tert-butyl hypoiodite (t-BuOI) or N-iodosuccinimide (NIS), enabling secondary non-benzylic and tertiary C?H amination reactions to proceed. The cyclic sulfamide products can be easily transformed into 1,3-diamines. Mechanistic investigations revealed that amination reactions using t-BuOI or NIS each proceed via different pathways.
- Kiyokawa, Kensuke,Jou, Keisuke,Minakata, Satoshi
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supporting information
p. 13971 - 13976
(2021/08/30)
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- Selective Synthesis of Secondary Amines from Nitriles by a User-Friendly Cobalt Catalyst
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Selective hydrogenation/reductive amination of nitriles to secondary amines catalyzed by an inexpensive and user-friendly cobalt complex, (Xantphos)CoCl2, is reported. The use of (Xantphos)CoCl2 and ammonia borane (NH3?BH3) combination affords the selective reduction of nitriles to symmetrical secondary amines, whereas the employment of (Xantphos)CoCl2 and dimethylamine borane (Me2NH?BH3) along with external amines produce unsymmetrical secondary amines and tertiary amines. The general applicability of this methodology is demonstrated by the synthesis of 43 symmetrical and unsymmetrical secondary and tertiary amines bearing diverse functionalities. (Figure presented.).
- Sharma, Dipesh M.,Punji, Benudhar
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supporting information
p. 3930 - 3936
(2019/07/12)
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- NHC-based coordination polymers as solid molecular catalysts for reductive amination of biomass levulinic acid
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A class of robust solid molecular NHC-based catalysts were readily fabricated via self-assembly from a p-phenylene-bridged bis-benzimidazolium salt with selected metal precursors. Among them, the NHC-Ru polymer demonstrated high catalytic activity and excellent stability as a solid molecular catalyst for the solvent-free reductive amination of biomass levulinic acid with inexpensive ammonium formate, furnishing a challenging unprotected 5-methyl-2-pyrrolidone quantitatively at a 0.15 mol% catalyst loading. The solid catalyst was readily recovered and reused for 37 runs without obvious loss of activity. Remarkably, a TON value up to 6.7 × 104 was achieved in a molar-scale reaction with a catalyst loading at 0.001 mol%. Inspired by the results of a preliminary mechanistic study, notably, one-pot tandem reductive reactions of LA with aldehydes or ketones were successfully developed, affording a variety of structurally intriguing and functional N-substituted 5-methyl-2-pyrrolidones in high chemo-selectivity with good to excellent yields.
- Sun, Zheming,Chen, Jiangbo,Tu, Tao
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p. 789 - 794
(2017/08/18)
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- A highly active cyclometallated iridium catalyst for the hydrogenation of imines
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A cyclometallated iridium complex containing an imino ligand has been shown to catalyse the hydrogenation of imines. The catalyst is highly active and selective for imino bonds, with a wide variety of imines being hydrogenated in less than 1 hour at a substrate/catalyst (S/C) ratio of 2000 at 20 bar H 2 pressure and 75 °C.
- Villa-Marcos, Barbara,Tang, Weijun,Wu, Xiaofeng,Xiao, Jianliang
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supporting information
p. 6934 - 6939
(2013/10/08)
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- Efficient preparation of N-benzyl secondary amines via benzylamine-borane mediated reductive amination
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An efficient one-pot reductive amination protocol for preparing N-benzyl secondary amines is described.
- Peterson, Matt A.,Bowman, Adam,Morgan, Sarah
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p. 443 - 448
(2007/10/03)
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- Borohydride exchange resin, a new reducing agent for reductive amination
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Borohydride Exchange Resin is a useful, convenient reducing agent for the reductive amination of aldehydes and ketones in alcoholic solvent.
- Yoon,Kim,Son,Choi
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p. 1595 - 1599
(2007/10/02)
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