Phosphine-based redox catalysis in the direct traceless Staudinger ligation of carboxylic acids and azides.
نویسندگان
چکیده
The synthesis of amide C N bonds through nucleophilic acyl substitutions constitutes one of the most fundamental transformations in chemical synthesis. Recently, the Staudingertype ligation of carboxylic acid derivatives (e.g., acid chlorides, anhydrides, acyl selenides, and thioesters) and azides has become a preeminent strategy for amide C N bond construction (Scheme 1a). However, the generation of
منابع مشابه
Synthesis of coumarin or ferrocene labeled nucleosides via Staudinger ligation
BACKGROUND Reaction of azides with triaryl phosphines under mild conditions gives iminophosphoranes which can react with almost any kind of electrophilic reagent, e.g. aldehydes/ketones to form imines or esters to form amides. This so-called Staudinger ligation has been employed in a wide range of applications as a general tool for bioconjugation including specific labeling of nucleic acids. ...
متن کاملA phosphine-mediated conversion of azides into diazo compounds.
N2 the mild: Diazo compounds are extremely versatile intermediates for synthetic organic chemistry, but their synthesis can be challenging in the presence of delicate functional groups. The Staudinger ligation has inspired a mild method for the conversion of a broad range of azides into their diazo compound derivatives through an acyl triazene intermediate.
متن کاملCarboxylic Acids as A Traceless Activation Group for Conjugate Additions: A Three-Step Synthesis of (±)-Pregabalin
The direct application of carboxylic acids as a traceless activation group for radical Michael additions has been accomplished via visible light-mediated photoredox catalysis. Photon-induced oxidation of a broad series of carboxylic acids, including hydrocarbon-substituted, α-oxy, and α-amino acids, provides a versatile CO2-extrusion platform to generate Michael donors without the requirement f...
متن کاملWater-soluble phosphinothiols for traceless staudinger ligation and integration with expressed protein ligation.
The traceless Staudinger ligation is an effective means to synthesize an amide bond between two groups of otherwise orthogonal reactivity: a phosphinothioester and an azide. An important application of the Staudinger ligation is in the ligation of peptides at a variety of residues. Here, we demonstrate that the traceless Staudinger ligation can be achieved in water with a water-soluble reagent....
متن کاملCoulombic effects on the traceless Staudinger ligation in water.
The traceless Staudinger ligation can be mediated by phosphinothiols under physiological conditions. Proximal positive charges are necessary to achieve that transformation, presumably because those charges discourage protonation of the key iminophosphorane intermediate. Here, a series of cationic phosphinothiols is used to probe Coulombic effects on the traceless Staudinger ligation in aqueous ...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Angewandte Chemie
دوره 51 48 شماره
صفحات -
تاریخ انتشار 2012