6391-89-5Relevant academic research and scientific papers
Preparation of alkylated compounds using the trialkylphosphate
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Paragraph 0184-0185; 0187, (2021/11/02)
[Problem] trialkylphosphate strong base used reaction agent, a carboxylic acid, a ketone, an aldehyde, amine, amide, thiol, ester or Grignard reagent to a variety of substrates, and/or high efficiency to generate a highly stereoselective alkylation reaction, the alkylated compounds capable of producing new means. [Solution] was used as the alkylating agent in the alkylation of compound trialkylphosphate, strongly basic reaction production use. [Drawing] no
Regio- And Stereoselective (S N2) N -, O -, C - And S -Alkylation Using Trialkyl Phosphates
Banerjee, Amit,Hattori, Tomohiro,Yamamoto, Hisashi
, (2021/06/16)
Bimolecular nucleophilic substitution (S N 2) is one of the most well-known fundamental reactions in organic chemistry to generate new molecules from two molecules. In principle, a nucleophile attacks from the back side of an alkylating agent having a suitable leaving group, most commonly a halide. However, alkyl halides are expensive, very harmful, toxic and not so stable, which makes them problematic for laboratory use. In contrast, trialkyl phosphates are inexpensive, readily accessible and stable at room temperature, under air, and are easy to handle, but rarely used as alkylating agents in organic synthesis. Here, we describe a mild, straightforward and powerful method for nucleophilic alkylation of various N -, O -, C - and S -nucleophiles using readily available trialkyl phosphates. The reaction proceeds smoothly in excellent yield, and quantitative yield in many cases, and covers a wide range of substrates. Further, the rare stereoselective transfer of secondary alkyl groups has been achieved with inversion of configuration of chiral centers (up to 98% ee).
Nickel(0)-Catalyzed N-Allylation of Amides and p-Toluenesulfonamide with Allylic Alcohols under Neat and Neutral Conditions
Azizi, Mohamed Salah,Edder, Youssef,Karim, Abdallah,Sauthier, Mathieu
, p. 3796 - 3803 (2016/08/16)
Nickel(0)-catalyzed direct N-allylation of amides and p-toluenesulfonamide with allylic alcohols took place in the presence of Ni0–diphosphine complexes. The corresponding N-allylated (and/or N,N-diallylated) products were obtained in moderate to high yields under neutral conditions.
AlMe3-promoted formation of amides from acids and amines
Li, Jianqing,Subramaniam, Krishnananthan,Smith, Daniel,Qiao, Jennifer X.,Li, Jie Jack,Qian-Cutrone, Jingfang,Kadow, John F.,Vite, Gregory D.,Chen, Bang-Chi
supporting information; experimental part, p. 214 - 217 (2012/02/16)
In the presence of AlMe3, amines can be directly coupled with acids through dimethylaluminum amide intermediates to form the corresponding amides. A wide range of amines and acids including less nucleophilic amines, bulky amines, unprotected se
A new convenient method to obtain pyrroles from tertiary N-allylthioamides
Magedov, Igor V.,Kornienko, Alexander V.,Zotova, Tatyana O.,Drozd, Victor N.
, p. 4619 - 4622 (2007/10/02)
1,2-Disubstituted pyrroles 1 were synthesized from available thioamides 4. Thioamides were initially treated with either alkylating agents or Lewis acids to give salts 5 or complexes 12 which were subsequently reacted with base to yield pyrroles 1.
A SIMPLE AND ECONOMICAL METHOD FOR THE ALKYLATION OF BENZANILIDES
Ayyangar, N. R.,Choudhary, A. R.,Kalkote, U. R.,Natu, A. A.
, p. 2011 - 2016 (2007/10/02)
A convenient and economically feasible method for the alkylation of benzanilides using tetra-n-butyl hydrogen sulphate phase transfer catalyst, powdered NaOH and anhydrous K2CO3 is described.
REARRANGEMENT OF ALLYLIC N-PHENYLFORMIMIDATES TO N-ALLYL-N-PHENYLFORMAMIDES CATALYZED BY PALLADIUM COMPLEXES
Ikariya, Takao,Ishikawa, Yasutoshi,Hirai, Kiyomiki,Yoshikawa, Sadao
, p. 1815 - 1818 (2007/10/02)
The palladium complexes such as Pd(PPh3)4 and Pd(PhCN)2Cl2 catalyzed the rearrangement of allylic N-phenylformimidates to give N-allyl-N-phenylformamides under a mild condition.The reaction courses are strongly influenced by the oxidation state of palladi
