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  • Redox-neutral α-C-H bond functionalization of secondary amines with concurrent C-P bond formation/N-alkylation.

Redox-neutral α-C-H bond functionalization of secondary amines with concurrent C-P bond formation/N-alkylation.

Organic letters (2013-08-21)
Deepankar Das, Daniel Seidel
ABSTRACT

Redox-neutral formation of C-P bonds in the α-position of amines was achieved via a process that features a combination of an oxidative α-C-H bond functionalization and a reductive N-alkylation. Benzoic acid functions as an efficient catalyst in this three-component reaction of cyclic secondary amines, aldehydes and phosphine oxides to provide rapid access to α-amino phosphine oxides not easily accessible by classic Kabachnik-Fields reactions.

MATERIALS
Product Number
Brand
Product Description

Supelco
Mettler-Toledo Calibration substance ME 18555, Benzoic acid, analytical standard, (for the calibration of the melting point system), traceable to primary standards (LGC)
Sigma-Aldrich
Benzoic acid, SAJ first grade, ≥99.5%
Sigma-Aldrich
Benzoic acid, SAJ special grade, ≥99.5%
Sigma-Aldrich
Potassium benzoate, ReagentPlus®, 99%
Sigma-Aldrich
Benzoic acid, ≥99.5%, FCC, FG
Sigma-Aldrich
Benzoic acid, ReagentPlus®, 99%
Sigma-Aldrich
Benzoic acid, natural, ≥99.5%, FCC, FG
Sigma-Aldrich
Benzoic acid, purified by sublimation, ≥99%
Sigma-Aldrich
Benzoic acid, ACS reagent, ≥99.5%
Supelco
Benzoic acid, Pharmaceutical Secondary Standard; Certified Reference Material
Supelco
Melting point standard 121-123°C, analytical standard
Supelco
Benzoic acid, Standard for quantitative NMR, TraceCERT®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland
Sigma-Aldrich
Benzoic acid, puriss. p.a., ACS reagent, reag. Ph. Eur., ≥99.9% (alkalimetric)
Supelco
Benzoic acid, reference material for titrimetry, certified by BAM, >99.5%
Sigma-Aldrich
Benzoic acid, meets analytical specification of Ph. Eur., BP, USP, FCC, E210, 99.5-100.5% (alkalimetric)