Haloalkenyl Imidoyl Halides as Multifacial Substrates in the Stereoselective Synthesis of N-Alkenyl Compounds

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F21%3A00541416" target="_blank" >RIV/61388963:_____/21:00541416 - isvavai.cz</a>

Alternative codes found

RIV/00216208:11310/21:10439265

Result on the web

<a href="https://doi.org/10.1002/adsc.202100009" target="_blank" >https://doi.org/10.1002/adsc.202100009</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/adsc.202100009" target="_blank" >10.1002/adsc.202100009</a>

Result language

angličtina

Original language name

Haloalkenyl Imidoyl Halides as Multifacial Substrates in the Stereoselective Synthesis of N-Alkenyl Compounds

Original language description

N-Alkenyl compounds are versatile synthetic building blocks and their stereoselective transformations are key processes in the synthesis of many prominent classes of natural products, pharmaceuticals, and agrochemicals. However, a large structural variety of known N-alkenyl compounds and their diverse reactivity have so far precluded the development of a general method for their stereoselective synthesis. Herein we present an aluminum halide-mediated, highly stereoselective, efficient and scalable transformation of commercially available N-fluoroalkyl-1,2,3-triazoles to N-haloalkenyl imidoyl halides, and demonstrate their use in the synthesis of stereodefined N-alkenyl amides, amidines, imines, hydrazonoamides, imidothioates, iminophosphonates, 1,2,4-triazoles and tetrazoles. The reaction is of wide scope on both the triazole substrate and aluminum halide, providing highly functionalized products. Mechanistic and computational investigations suggest a reaction mechanism involving the triazole ring opening, initiated by the coordination of nitrogen one of the triazole ring to the Lewis acid, N2 elimination and the formation of a vinyl cation intermediate, which reacts with nitrogen-bound aluminum halide, followed by a series of halide exchange reactions on C−X and Al−X bonds. (Figure presented.).

Czech name

—

Czech description

—

Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

—

OECD FORD branch

10401 - Organic chemistry

Project

<a href="/en/project/LTAUSA18037" target="_blank" >LTAUSA18037: Synthesis and reactivity of N-fluoroalkylated compounds</a><br>

Continuities

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year

2021

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Advanced Synthesis & Catalysis

ISSN

1615-4150

e-ISSN

1615-4169

Volume of the periodical

363

Issue of the periodical within the volume

13

Country of publishing house

DE - GERMANY

Number of pages

9

Pages from-to

3258-3266

UT code for WoS article

000625420400001

EID of the result in the Scopus database

2-s2.0-85101981506