Dess-Martin reagent

CAS 87413-09-0, Cat. No EN300-66581

Oxidizing reagent

The Dess-Martin reagent is a widely utilized oxidant, effectively transforming 1° and 2° alcohols into aldehydes and ketones. Presenting as a stable white powder, it exhibits a melting point ranging from 103 to 133 ℃^[1]. The Dess-Martin reagent offers key advantages over chromium- and DMSO-based oxidants. These benefits encompass milder reaction conditions (at room temperature and neutral pH), abbreviated reaction times, elevated yields, simplified purification steps, exceptional chemoselectivity, and compatibility with sensitive functional groups^[2]. Usually, the reaction is conducted in DCM or chloroform but can be performed in DMSO, DMF, and EtOAc. Using the standard Dess–Martin periodinane conditions, alcohols can be oxidized to aldehydes/ketones without affecting furan rings, sulfides, vinyl ethers, and secondary amides^{[1], [2]}. Allylic alcohols, which are typically difficult to convert to their respective carbonyls using the typical oxidants, are easily oxidized using DMP. Also, it can oxidize N-protected amino alcohols without epimerization (unlike most other oxidants, including Swern oxidation).

Synonyms: Dess-Martin reagent, Dess-Martin Periodinane reagent, or Dess-Martin oxidant, 1,2-Benziodoxol-3(1H)-one, 1,1,1-tris(acetyloxy)-1,1-dihydro- (9CI), (1,1-Diacetoxy-3-oxo-1,2-benziodoxol-1-yl) acetate, 1,1,1-Triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one, 1,1,1-Tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3(1H)-on, 3-Oxo-1λ,2-benziodoxole-1,1,1(3H)-triyl triacetate

Selected publication

1. 1,1,1-Triacetoxy-1,1-Dihydro-1,2-Benziodoxol-3(1 H )-One.

Boeckman R. J.; George K. M. Encyclopedia of Reagents for Organic Synthesis 2009. DOI: 10.1002/047084289X.rt157m.pub2

2. Dess-Martin reagent.

Wang Z. Comprehensive Organic Name Reactions and Reagents 2010. DOI: 10.1002/9780470638859