AMBIDENT REACTIVITY OF P=CH-N-HETEROCYCLES: LITHIATION AND SUBSTITUTION SITES

作者：Heinicke Joachim^*; Aluri Bhaskar R; Niaz Basit; Burck Sebastian; Gudat Dietrich; Niemeyer Mark; Holloczki Oldamur; Nyulaszi Laszlo; Jones Peter G

来源：Phosphorus, Sulfur, and Silicon and the Related Elements, 2011, 186(4): 683-687.

DOI：10.1080/10426507.2010.514486

• Ambident reactivity
• hybrid ligands
• lithiation
• phosphinylation
• phosphenes
• phosphorus heterocycles

Benzofused 1H-1,3-azaphospholes are lithiated at the N-atom by tBuLi but phosphinylation takes place at either the N- or the P-atom. Smaller chlorophosphines react at nitrogen, bulkier react at phosphorus. Substituents at C2 promote the latter mode. N- Substituted 2H-1,3-benzazaphospholes undergo CH-metalation or addition at the P=C bond, depending on the conditions, and allow access to 2-functionally substituted benzazaphospholes or their 2,3-dihydro derivatives, new sigma(2)P,X or sigma(3)P,X hybrid ligands (X=O,P).

• 出版日期2011