Methyl-α-d-glucopyranoside as Green Ligand for Selective Copper-Catalyzed N-Arylation

Synthesis ◽  
2019 ◽  
Vol 51 (24) ◽  
pp. 4590-4600
Author(s):  
Yuanguang Chen ◽  
Fangyu Du ◽  
Fengyang Chen ◽  
Qifan Zhou ◽  
Guoliang Chen

In the selective N-arylation of amines or azoles with aryl halides­, methyl-α-d-glucopyranoside (MG) was found to function as a green ligand of copper powder. In addition, nitrogen heterocyclic amine compounds can also undergo the N-arylation coupling with heterocyclic aryl chlorides. This process allows access to a variety of aromatic amines and aryl azoles under mild reaction conditions, has good tolerance, and proceeds in moderate to high yield.

Synthesis ◽  
2018 ◽  
Vol 50 (23) ◽  
pp. 4617-4626 ◽  
Author(s):  
Ken-ichi Fujita ◽  
Genki Toyooka ◽  
Akiko Tuji

Efficient and versatile catalytic systems were developed for the N-methylation of both aliphatic and aromatic primary amines using methanol as the methylating agent. Iridium complexes bearing an N-heterocyclic carbene (NHC) ligand exhibited high catalytic performance for this type of transformation. For aliphatic amines, selective N,N-dimethylation was achieved at low temperatures (50–90 °C). For aromatic amines, selective N-monomethylation and selective N,N-dimethylation were accomplished by simply changing the reaction conditions (presence or absence of a base with an appropriate catalyst). These findings can be used to develop methods for synthesizing useful amine compounds having N-methyl or N,N-dimethyl moieties.


2018 ◽  
Author(s):  
Victor Laserna ◽  
Tom Sheppard

A versatile approach to the valorization of propargylic alcohols is reported, enabling controlled access to three different products from the same starting materials. Firstly, a general method for the hydroamination of propargylic alcohols with anilines is described using gold catalysis to give 3-hydroxy imines with complete regioselectivity. These 3-hydroxyimines can be reduced to give 1,3-aminoalcohols with high syn seletivity. Alternatively, by using a catalytic quantity of aniline, 3-hydroxyketones can be obtained in high yield directly from propargylic alcohols. Further manipulation of the reaction conditions enables the selective formation of 3-aminoketones via a rearrangement/hydroamination pathway.<br>


1992 ◽  
Vol 57 (2) ◽  
pp. 393-396 ◽  
Author(s):  
Martin Kotora ◽  
Milan Hájek

The 2 : 1 adduct as the final product of the addition of tetrachloromethane to 1,5-hexadiene catalyzed by copper(I)-butylamine complex was obtained in high yield (96%) under mild reaction conditions. Predominant 1 : 1 adduct formation was observed in the presence of a palladium catalyst or dibenzoyl peroxide initiator.


2017 ◽  
Vol 41 (3) ◽  
pp. 168-171 ◽  
Author(s):  
Zheng Li ◽  
Jiasheng Li ◽  
Jingya Yang

Seventeen examples of 2,6-diarylspiro[cyclohexane-1,3′-indoline]-2′4-diones were efficiently prepared by the Cs2CO3-catalysed chemoselective double Michael additions of indolin-2-one to divinyl ketones. This method has the advantage of high chemoselectivity, mild reaction conditions, high yield and atom- and step-economy.


2007 ◽  
Vol 2007 (8) ◽  
pp. 486-489 ◽  
Author(s):  
Mahmood Tajbakhsh ◽  
Setareh Habibzadeh

1,4-Diazabicyclo[2,2,2]octane (DABCO) is easily chlorinated and gives a complex which efficiently converts aliphatic and aromatic oximes, phenylhydrazones and semicarbazones to their corresponding carbonyl compounds in water at 50°C in high yield. This reagent can also be used for conversion of thiols to their compounding disulfide under the same reaction conditions. DABCO is quantitatively recovered which can be rechlorinated and reused several times.


2010 ◽  
Vol 88 (9) ◽  
pp. 964-968 ◽  
Author(s):  
Zhaoqiong Jiang ◽  
Zhiqing Wu ◽  
Lixia Wang ◽  
Di Wu ◽  
Xiangge Zhou

A simple, highly efficient, and environmentally friendly protocol for the synthesis of primary aromatic amines by catalytic coupling of aromatic boronic acids with aqueous ammonia has been developed by using commercial and inexpensive CuSO4·5H2O as catalyst without addition of other solvents under mild reaction conditions.


1979 ◽  
Vol 57 (16) ◽  
pp. 2114-2117 ◽  
Author(s):  
John M. McIntosh

Regiospecific formation of 10-allyl-1-ketoquinolizidine (7) is achieved in high yield by a [2.3] sigmatropic rearrangement of N-allyl-1-ketoquinolizidinium bromide (6). Wolff–Kischner reduction of 7 affords 10-allylquinolizidine (8) contaminated by the 10-propyl and 10-ethynyl analogs in amounts which depend on the reaction conditions. The carbon-13 spectrum of 8 indicates a trans-fused ring system with an axial substituent at C-10.


1983 ◽  
Vol 38 (6) ◽  
pp. 793-794 ◽  
Author(s):  
Armand Blaschette ◽  
Gerlinde Seurig

AbstractTetramethylsilane reacts with HN(SO2Cl)2 (1) in a complex manner, the nature of the product mixture depending strongly on the reaction conditions. Refluxing 1 with TMS in excess, using CH2Cl2 as a diluent, affords in high yield the new compound HN(SO2Cl)(SO2Me) (2) according to eq. (3). Hydrolysis of the crystal-line, moisture sensitive compound 2 is described by eq. (4).


2020 ◽  
Vol 10 (2) ◽  
pp. 66
Author(s):  
. HASNAM ◽  
EMY SULISTYOWATI ◽  
SIWI SUMARTINI ◽  
FITRINTNGDYAH TRI KADARWATI ◽  
PRIMA D. RIAJAYA

<p>Tujuan utama pemuliaan kapas di Indonesia adalah meningkatkan produktivitas dan kualitas serat dalam upaya meningkatkan pendapatan petani dan memperbaiki mutu benang tcnun seta kualitas tekstil yang harus bersaing di pasar internasional. Scjumlah enam persilangan telah dilakukan antara dua varietas dai India. I.RA 5166 dan SRT-1 dengan dua varietas dai Amerika Serikat, Dcltapine 55 dan Deltapinc Acala 90 dan satu vaietas dai Australia, Siokra. Seleksi individu, seleksi galur dan seleksi individu dalam galur dilaksanakan pada generasi F2 sampai F5 berdasarkan jumlah buah, tingkat kerusakan daun terhadap Sundapteryx biguttula. dan mutu serat; semua proses di atas dilakukan pada kondisi lahan tadah hujan, dan tanpa penggunaan insektisida terhadap tanaman; dari proses di atas diperoleh 12 galur harapan. Sejumlah 13 percobaan dilakukan antara tahun 1993 sampai dengan 2001 untuk mengamati kcragaan galur-galur baru tersebut; pengujian dilakukan di Jawa Timur dan Sulawesi Selatan, menggunakan teknik-teknik penelitian standar. Dengan proscdur ini dapat diidcntifikasi beberapa galur yang menunjuk¬ kan perbaikan serenlak hasil dan kualitas serat kapas. Beberapa penelitian juga dilakukan untuk mcngcvaluasi tanggap galur-galur tersebut pada tumpangsari dengan kedelai dan kacang hijau di Jawa Timur. Dua galur, 88003/16/2 dan 92016/6 (sudah dilepas dengan nama vaietas Kanesia 8 dan Kanesia 9 pada bulan Juni 2003), menunjukkan produktivitas dan kualitas serai yang lebih linggi. Rata-rata, kedua vaietas menghasilkan 1.85 ton dan 191 ton kapas berbiji per hektar atau 8-12% lebih tinggi dai hasil vaietas Kanesia 7 yang sudah dilepas sebelumnya. Persentase serat 35.2%, kekuatan serat berkisar antara 22.6-24.7 gram tex'1, serat lebih panjang dan berkisar 29.2-30.3 mm sedangkan angka mikroncr lebih rendah yang menyatakan bahwa serat lebih halus. Semua perbaikan di atas menunjukkan perbaikan mutu serat. Kanesia 8 dan Kanesia 9 juga menunjukkan peningkatan ketahanan terhadap Sundapteryx biguttula dan komplcks hama kapas. Kanesia 8 dan Kanesia 9 kurang kompctitif dalam tumpang sari dengan kedelai jika dibandingkan dengan Kanesia 7. Pada tumpang sari dengan kacang hijau Kanesia 8 juga mengalami kehilangan hasil yang tinggi, sedangkan Kanesia 9 menunjukkan toleransi yang tinggi dalam kompctisi dengan kacang hijau. Pelepasan Kanesia 8 dan Kanesia 9 akan memberikan pilihan varietas yang lebih banyak bagi petani dan perusahaan pemintalan untuk menyesuaikan dengan produk akhirnya.</p><p>Kata kunci : Gossypium hirsutum, prosedur pemuliaan, produktivitas, kualitas serat, Sundapteryx biguttula, tumpangsari</p><p> </p><p><strong>ABSTRACT </strong></p><p><strong>Genetic improvement on two new cotton varieties, Kanesia 8 and Kanesia 9</strong></p><p>The main objective of cotton breeding in Indonesia is to improve productivity and fiber quality which is aimed to increase farmers' income and to make beter yam and textile quality that has to compete in international market Six crosses were made between two Indian varieties, LRA 5166 and SRT-1 with two USA vaieties, Deltapine 55 and Deltapinc Acala 90 and one Australian variety, Siokra. Individual plants, lines and individual within lines were selected on F2-F5 generations based on boll- counts, leaf-damage by jassids and fiber traits, those were conducted under rainfed and insecticide-ree condition; twelve promising lines were produced from this process. A total of 13 trials were carried out to observe performance of these new lines during 1993 to 2001; those were located in East Java and South Sulawesi using the standardized experimental techniques. By these procedures make it possible to identify several breeding lines showing simultaneous improvement in yield and fiber quality. Several tests were also made to evaluate response of those lines under intercropping with soybean and mungbean, which were located in East Java. Two breeding lines, 88003/16/2 and 92016/6 (those have been released as Kanesia 8 and Kanesia 9 in 2003), showed higher productivity and fiber quality. In average, these new vaieties produced 1.85 and 1.91 ton ha'1 seed cotton respectively or 8 to 12% higher than those on Kanesia 7, the previously released vaiety. Lint turn-out was 35.2% fiber-strength was varied from 22.6 to 24.7 gram tex'1 , fiber lengths ranged from 29.2 to 30.3 mm with lower micronaire-valucs indicating better fiber-ineness. All of those improvements represented a trend toward a higher quality iber. Kanesia 8 and Kanesia 9 also showed a slight improvement in resistance to jasssids and insect pest-complex. Kanesia 8 and Kanesia 9 performed lower competitive ability under intercropping with soybean in comparison with Kanesia 7. Under intercropping with mungbean Kanesia 8 also suffered high yield loss, wherein Kanesia 9 showed good tolerance to mungbean. The release of Kanesia 8 and Kanesia 9 is expected to give a broader choice for the cotton growers and spinning-mills to match with their inal product.</p><p>Key words: Coton (Gossypium hirsutum), breeding procedure, productivity, liber quality, Sundapteryx bigullul. inter¬ cropping.</p>


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