๐”– Bobbio Scriptorium
โœฆ   LIBER   โœฆ

Aromatic substitution via organoboranes 2. Regiospecific alkylation of the furan and pyrrole nucleus

โœ Scribed by Edmund R. Marinelli; Alan B. Levy

Publisher
Elsevier Science
Year
1979
Tongue
French
Weight
235 KB
Volume
20
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

โœฆ Synopsis

Swrunary: Reaction of 2-lithiofuran or 1-methyl-2-lithiopyrrole with trialkylboranes leads to a borate salt. Subsequent treatment with an appropriate electrophile such as NCS leads to the 2alkylfuran or 1-methyl-2-alkylpyrrole.

Electrophilic substitution is among the most important methods known for the functionalization of benzene and related aromatic derivatives.

1 In sharp contrast, heteroaromatics show variable response in electrophilic substitution reactions.

2 Furans and pyrroles, in particular, respond poorly to typical Friedal-Crafts conditions. Instead, nonselective substitution, polymerization or ring destruction is usually observed.

We have recently demonstrated3 a novel method for regiospecifically substituting the indole nucleus at the two-position via organoboranes (eq 1).

-In principle, this methodology should be mLi + RBR"2

๐Ÿ“œ SIMILAR VOLUMES

Synthesis of 2-Substituted Pyridines via
Synthesis of 2-Substituted Pyridines via a Regiospecific Alkylation, Alkynylation, and Arylation of Pyridine N-Oxides.
โœ Hans Andersson; Fredrik Almqvist; Roger Olsson ๐Ÿ“‚ Article ๐Ÿ“… 2007 ๐Ÿ› John Wiley and Sons โš– 30 KB

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.