Photoredox B–H Functionalization to Selective B–N(sp3) Coupling of nido-Carborane with Primary and Secondary Amines

2021 ◽  
Author(s):  
Hong Yan ◽  
Changsheng Lu ◽  
Ronghui Huang ◽  
Weijia Zhao ◽  
Shengwen Xu ◽  
...  
Keyword(s):  
Secondary Amines ◽  
Primary And Secondary Amines ◽  
Site Selective ◽  
First Time

Access to nido-carborane site-selective B–N(sp3) coupling by photoredox catalyzed B–H activation has been achieved for the first time, which leads to the synthesis of a series of nitrogen-containing nido-carboranes in...

Cobalt/Lewis Acid Catalysis for Hydrocarbofunctionalization of Alkynes via Cooperative C–H Activation

2020 ◽  
Author(s):  
Chang-Sheng Wang ◽  
Sabrina Monaco ◽  
Anh Ngoc Thai ◽  
Md. Shafiqur Rahman ◽  
Chen Wang ◽  
...  
Keyword(s):  
Catalytic System ◽  
Lewis Acid ◽  
Hydrogen Transfer ◽  
Acid Catalysis ◽  
Rate Limiting Step ◽  
Site Selectivity ◽  
Set Up ◽  
Site Selective ◽  
First Time ◽  
Rate Limiting

A catalytic system comprised of a cobalt-diphosphine complex and a Lewis acid (LA) such as AlMe3 has been found to promote hydrocarbofunctionalization reactions of alkynes with Lewis basic and electron-deficient substrates such as formamides, pyridones, pyridines, and azole derivatives through site-selective C-H activation. Compared with known Ni/LA catalytic system for analogous transformations, the present catalytic system not only feature convenient set up using inexpensive and bench-stable precatalyst and ligand such as Co(acac)3 and 1,3-bis(diphenylphosphino)propane (dppp), but also display distinct site-selectivity toward C-H activation of pyridone and pyridine derivatives. In particular, a completely C4-selective alkenylation of pyridine has been achieved for the first time. Mechanistic stidies including DFT calculations on the Co/Al-catalyzed addition of formamide to alkyne have suggested that the reaction involves cleavage of the carbamoyl C-H bond as the rate-limiting step, which proceeds through a ligand-to-ligand hydrogen transfer (LLHT) mechanism leading to an alkyl(carbamoyl)cobalt intermediate.

Reaction of arylmethylenemalonaldehydes with some nucleophiles

1987 ◽  
Vol 52 (11) ◽  
pp. 2699-2709 ◽  
Author(s):  
Dalimil Dvořák ◽  
Zdeněk Arnold
Keyword(s):  
Inorganic Anions ◽  
Secondary Amines ◽  
Tertiary Amines ◽  
Primary And Secondary Amines ◽  
Dipolar Structure

Reaction of arylmethylenemalonaldehydes with tributylphosphine and tertiary amines affords compounds of dipolar structure whereas reaction with primary and secondary amines leads to 1,4-addition products. Salts of nucleophilic inorganic anions add to arylmethylenemalonaldehydes under formation of salts of substituted malonaldehydes.

Some 1-substitution derivatives of 4-aryl-2,3-dihalogeno-1-naphthols

1984 ◽  
Vol 49 (1) ◽  
pp. 110-121 ◽  
Author(s):  
Jiří Křepelka ◽  
Drahuše Vlčková ◽  
Milan Mělka
Keyword(s):  
Thionyl Chloride ◽  
Oxirane Ring ◽  
Secondary Amines ◽  
Two Phase ◽  
Lytic Effect ◽  
Primary And Secondary Amines ◽  
Phase Medium ◽  
Chloro Derivatives ◽  
Derivatives Of

Alkylation of derivatives of 4-aryl-1-naphthols (I-V) by 2,3-epoxypropyl chloride in methanolic sodium hydroxide gave epoxy derivatives VI, VIII, IX, XI and XII, apart from products of cleavage of the oxirane ring, VII and X. Analogous alkylation of compounds I, IV and V by 2-(N,N-diethylamino)ethyl chloride hydrochloride in a two-phase medium afforded basic ethers XIII to XV. The cleavage of the oxirane ring in compound VI by the action of primary and secondary amines, piperidine and substituted piperazines led to compounds XVI-XXIV. Reaction of thionyl chloride with compounds XXI, XXII and XXIV gave chloro derivatives XXV-XXVII.Exposure of compound XXII to 4-methylbenzenesulfonyl chloride produced compound XXVIII, retaining the secondary alcoholic group. In an antineoplastic screening in vivo none of the compounds prepared had an appreciable activity. Compound XVII, being an analogue of propranolol, was used in the test of isoproterenolic tachycardia, and showed a beta-lytic effect comparable with that of propranol.

ChemInform Abstract: Continuous-Flow Oxidative Cyanation of Primary and Secondary Amines Using Singlet Oxygen.

ChemInform ◽  
2014 ◽  
Vol 45 (30) ◽  
pp. no-no
Author(s):  
Dmitry B. Ushakov ◽  
Kerry Gilmore ◽  
Daniel Kopetzki ◽  
D. Tyler McQuade ◽  
Peter H. Seeberger
Keyword(s):  
Singlet Oxygen ◽  
Continuous Flow ◽  
Secondary Amines ◽  
Primary And Secondary Amines

Catalytic alkyl group exchange reaction of primary and secondary amines

1983 ◽  
Vol 105 (15) ◽  
pp. 5002-5011 ◽  
Author(s):  
Shunichi Murahashi ◽  
Noriaki Yoshimura ◽  
Tatsuo Tsumiyama ◽  
Takeyuki Kojima
Keyword(s):  
Exchange Reaction ◽  
Alkyl Group ◽  
Secondary Amines ◽  
Primary And Secondary Amines

Direct amidation of carboxylic acids with amines under microwave irradiation using silica gel as a solid support

2015 ◽  
Vol 17 (5) ◽  
pp. 3157-3163 ◽  
Author(s):  
Andrea Ojeda-Porras ◽  
Alejandra Hernández-Santana ◽  
Diego Gamba-Sánchez
Keyword(s):  
Fatty Acids ◽  
Microwave Irradiation ◽  
Carboxylic Acids ◽  
Silica Gel ◽  
Solid Support ◽  
Secondary Amines ◽  
Primary And Secondary Amines ◽  
Direct Amidation

A highly improved methodology for the direct amidation of carboxylic acids with amines using silica gel as a solid support and catalyst is described. Several examples using aliphatic, aromatic, unsaturated and fatty acids combined with primary and secondary amines are shown.

ChemInform Abstract: Palladium-Catalyzed Coupling of Functionalized Primary and Secondary Amines with Aryl and Heteroaryl Halides: Two Ligands Suffice in Most Cases.

ChemInform ◽  
2011 ◽  
Vol 42 (15) ◽  
pp. no-no
Author(s):  
Debabrata Maiti ◽  
Brett P. Fors ◽  
Jaclyn L. Henderson ◽  
Yoshinori Nakamura ◽  
Stephen L. Buchwald
Keyword(s):  
Secondary Amines ◽  
Primary And Secondary Amines ◽  
Palladium Catalyzed

Direct ring-opening of lactide with amines: application to the organo-catalyzed preparation of amide end-capped PLA and to the removal of residual lactide from PLA samples

2015 ◽  
Vol 6 (6) ◽  
pp. 989-997 ◽  
Author(s):  
Aurélie Alba ◽  
Olivier Thillaye du Boullay ◽  
Blanca Martin-Vaca ◽  
Didier Bourissou
Keyword(s):  
Ring Opening ◽  
Secondary Amines ◽  
Primary And Secondary Amines

Spontaneous ring-opening of lactide by primary and secondary amines has been applied to the preparation of well-defined amide end-capped PLA and to the removal of unreacted lactide from PLA samples.

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