ChemInform Abstract: Diels—Alder Reactions with the <C=P—Functionality of Anellated Azaphospholes

Abstract

Diels-Alder Reactions with the >C=P-Functionality of Anellated Azaphospholes -[36 refs. + subrefs.]. -(BANSAL*, R. K.; GUPTA, R.; KOUR, M.; Synlett 26 (2015) 3, 294-303, http://dx.doi.org/10.1055/s-0034-1379708 ; Dep. Chem., IIS Univ., Jaipur 302 020, India; Eng.) -Y. Steudel 18-293

Access to Benzo‐ and Naphtho‐Azaphospholes via C−H Bond Activation of Aryl‐Substituted Isonitriles

“…Here we show that the biradical 2R is also capable of reacting with isonitriles under selective C−H activation to form novel benzo‐ and naphtho‐azaphospholes in a straightforward, high‐yielding procedure [47] . Finally, azaphospholes (with a condensed benzene ring also called phospha‐indoles), for which we have accidentally discovered a new synthesis, represent a class of compounds that has been extensively studied in terms of their preparation and further use [47–55] . For example, the classical routes to prepare these compounds start with o ‐amino‐phenyl phosphanes and involve the use of a cyclizing agent such as acid chlorides or esters (Scheme 2).…”

“…[47] Finally, azaphospholes (with a condensed benzene ring also called phospha-indoles), for which we have accidentally discovered a new synthesis, represent a class of compounds that has been extensively studied in terms of their preparation and further use. [47][48][49][50][51][52][53][54][55] For example, the classical routes to prepare these compounds start with oamino-phenyl phosphanes and involve the use of a cyclizing agent such as acid chlorides or esters (Scheme 2). [48,52,55] Other routes use variously substituted phenyl isonitriles as starting materials, and reaction with elemental lithium can yield the corresponding aza-phospholes (Scheme 2).…”