کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
5212916 1383138 2017 7 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Aminocarbonylation (hydrazinocarbonylation) of iodoalkenes and iodoarenes
ترجمه فارسی عنوان
آمینوکربنایلینگ (هیدرازین کربناتیک) یودوالکنه ها و یودواران ها
کلمات کلیدی
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
چکیده انگلیسی

Iodoalkenes such as 1-iodocyclohexene, 4-tert-butyl-1-iodocyclohexene, α-iodostyrene and 17-iodoandrost-16-ene were aminocarbonylated in palladium-catalysed reaction using 1,1-disubstituted (cyclic) hydrazines (3-amino-3-azabicyclo[3.3.0]octane and (S)-1-amino-2-methoxymethylpyrrolidine (SAMP)/(R)-1-amino-2-methoxymethyl-pyrrolidine (RAMP)) as N-nucleophiles. The corresponding hydrazides were formed in moderate to high yields. The hydrazinocarbonylation of iodobenzene using the above 1,1-disubstituted hydrazines resulted in a rather complex reaction mixture due to two major types of side-reactions: i) the deamination of the 3-amino-3-azabicyclo[3.3.0]octane, and ii) the double carbon monoxide insertion. In this way, in addition to the expected benzoylhydrazide derivative, phenylglyoxylhydrazide (double CO insertion product) and benzamide ('deamination' product) were also formed. By the appropriate modification of the reaction conditions, good selectivities towards the target compounds were achieved even in these cases. The formation of the products/side-products were rationalized on the basis of a simplified catalytic cycle.

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ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron - Volume 73, Issue 7, 16 February 2017, Pages 838-844
نویسندگان
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