One-pot primary aminomethylation of aryl and heteroaryl halides with sodium phthalimidomethyltrifluoroborate.

One-pot primary aminomethylation of aryl and heteroaryl halides with sodium phthalimidomethyltrifluoroborate.

Organic letters (2012-05-18)

Norio Murai, Masayuki Miyano, Masahiro Yonaga, Keigo Tanaka

ABSTRACT

A one-pot primary aminomethylation of aryl halides, triflates, mesylates, and tosylates via Suzuki-Miyaura cross-coupling reactions with sodium phthalimidomethyltrifluoroborate followed by deamidation with ethylenediamine is reported.

MATERIALS

Product Number

Brand

Product Description

83000

Sigma-Aldrich

Potassium methanesulfonate, ≥98.0% (dry substance, T)

304506

Sigma-Aldrich

Sodium methanesulfonate, 98%

M4141

Sigma-Aldrich

Methanesulfonic acid solution, 4 M (with 0.2% (w/v) tryptamine)

471348

Sigma-Aldrich

Methanesulfonic acid solution, 70 wt. % in H₂O

550256

Sigma-Aldrich

Silver methanesulfonate

471356

Sigma-Aldrich

Methanesulfonic acid, ≥99.0%

55517

Supelco

Methanesulfonic acid concentrate, 0.1 M CH₃SO₃H in water (0.1N), eluent concentrate for IC