687-09-2

Upstream product

• 111-26-2 hexan-1-amine 
• 407-25-0 trifluoroacetic anhydride 
• 96254-05-6 2-(trifluoroacetyloxy)pyridine 
• 36971-66-1 triphenylantimony bis(trifluoroacetate) 
• 76-05-1 trifluoroacetic acid 
• 86308-26-1 2-hex-1-yl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 592-41-6 1-hexene 

Downstream Products

• 111-26-2 hexan-1-amine 
• 75-89-8 2,2,2-trifluoroethanol 

Relevant academic research and scientific papers

Photoinduced remote regioselective radical alkynylation of unactivated C-H bonds

A method for the remote regioselective alkynylation of unactivated C(sp3)-H bonds in diverse aliphatic amides by photogenerated amidyl radicals has been developed. The site-selectivity is dominated via a 1,5-hydrogen atom transfer (HAT) process of the amide. Mild reaction conditions and high regioselectivity are demonstrated in this methodology.

Remote Regioselective Radical C-H Functionalization of Unactivated C-H Bonds in Amides: The Synthesis of gem-Difluoroalkenes

The site-selective functionalization of unactivated aliphatic amines is an attractive and challenging synthetic approach. We herein report a general strategy for the remote site-selective functionalization of unactivated C(sp3)-H bonds in amides by photogenerated amidyl radicals to form gem-difluoroalkenes with trifluoromethyl-substituted alkenes. The site selectivity is controlled by a 1,5-hydrogen atom transfer (HAT) process of the amide. This photocatalyzed transformation shows both chemo- and site-selectivity, facilitating the formation of a secondary, tertiary, or quaternary carbon center.

Site-Selective Defluorinative sp3C-H Alkylation of Secondary Amides

A site-selective defluorinative sp3 C-H alkylation of secondary amides that rapidly and reliably incorporates gem-difluoroalkene motifs into previously unfunctionalized sp3 sites is disclosed. This protocol is distinguished by its mild conditions, wide scope, and exquisite site-selectivity, thus unlocking a new platform to introduce carbonyl isosteres at saturated hydrocarbon sites.

Amination reagent as well as preparation method and application thereof

The invention discloses an amination reagent as well as a preparation method and application thereof. The amination reagent has a structure as shown in a formula disclosed in the invention, wherein Xis selected from any one of I, Cl, Br, NO3 and ClO4, and Y and Z are independently selected from H or alkyl with the carbon atom number of 1-4. The process for preparing the amination reagent is simple, the raw materials are easy to obtain, the cost is low, the yield is stable, and the prepared amination reagent is stable in character, can be stored at room temperature for a long time and can be taken as needed; meanwhile, the prepared amination reagent is efficient in performance, boron substrate applicability is excellent, reaction effect is good, and limitation of amination reaction of organic boron compounds on substrates is greatly expanded.

Aminoazanium of DABCO: An Amination Reagent for Alkyl and Aryl Pinacol Boronates

The aminoazanium of DABCO (H2N-DABCO) has been developed as a general and practical amination reagent for the direct amination of alkyl and aryl pinacol boronates. This compound is stable and practical for use as a reagent. Various primary, secondary. and tertiary alkyl?Bpin and aryl?Bpin substrates were aminated to give the corresponding amine derivatives. The amination is stereospecific. The anti-Markovnikov hydroamination of olefins was easily achieved by catalytic hydroboration with HBpin and in subsequent situ amination using H2N-DABCO. Moreover, the combination of 1,2-diboration of olefins, using B2pin2, with this amination process achieved the unprecedented 1,2-diamination of olefins. The amination protocol was also successfully extended to aryl pinacol boronates.

Regioselective Alkylative Cross-Coupling of Remote Unactivated C(sp3)-H Bonds

The functionalization of unactivated C(sp3)-H bonds poses a significant challenge due to their ubiquity and relative similarity in most organic frameworks. Herein, we describe the use of a combined photoredox and nickel catalytic system for the regioselective C(sp3)-C(sp3) coupling of unactivated C(sp3)-H bonds and alkyl bromides. Positional selectivity is dictated by a 1,5-hydrogen atom transfer (HAT) reaction by a pendent amide. Interception of this radical by a Ni catalyst allows distal alkylation to occur in good yield and excellent selectivity.

Transition metal-free intermolecular a-C-H amination of ethers at room temperature

We describe a new method for the intermolecular amination of the α-C-H bonds of ethers. A hypervalent iodine reagent was used as oxidant to enable the amination of cyclic and acyclic alkyl ethers with a wide range of amides, imides, and amines. The amination occurred at room temperature and without a transition metal catalyst. The method could be used to synthesize the anti-cancer prodrug Tegafur and its analogues.

Trifluoroacetylation of amines with trifluoroacetic acid in the presence of trichloroacetonitrile and triphenylphosphine

We developed a mild and convenient trifluoroacetylation process for amines using a combination of trichloroacetonitrile and triphenylphosphine. The reaction that we designed is applicable to the trifluoroacetylation of a wide variety of amines, including amines with stereogenic centers, which underwent trifluoroacetylation without racemization.

2-(Trifluoroacetyloxy)pyridine as a Mild Trifluoroacetylating Reagent of Amines and Alcohols

A new trifluoroacetylating reagent, 2-(trifluoroacetyloxy)pyridine (TFAP), was prepared by the reaction of 2-pyridinol and trifluoroacetic anhydride.TFAP has been found to be effective in the trifluoroacetylation of aliphatic and aromatic amines and alcohols including phenol under mild conditions.The reaction of p-nitrophenol with TFAP in ether gave the hydrogen-bonded complex between the phenol and 2-pyridone.This reagent has also been shown to be useful for the intramolecular dehydration of aldehyde oximes and amides to give nitriles in high yields.