Deconstructive Cycloaromatization Strategy toward N,O-Bidentate Ligands from Indolizines and Cyclopropenones

Abstract

The innovative construction of novel N,O-bidentate ligands represents a long-standing challenge for chemists. Here, we report an unprecedented approach for the construction of N,O-bidentate derivatives via the merging of ring deconstruction with cycloaromatization of indolizines and cyclopropenones. Without any catalysts, our method can deliver a series of polyaryl 2-(pyridin-2-yl)phenols in excellent yields. In addition, N,O-bidentate organic BF 2 complexes can also be constructed via this one-pot protocol.

Transition metal-free annulative vinylene transfer via the 1,3-dipolar reaction of N-ylides: access to benzo-fused indolizines

“…12,13 We have long been committed to the construction of indolizine derivatives. 14 As part of our continuous research, herein we report an efficient metal-free annulative vinylene transfer protocol for the synthesis of benzo-fused indolizines via [3 + 2] cycloadditions of N -ylides with vinylene carbonate (Scheme 1c).…”

Synthesis and Optical Properties of Polyaryl 2‐(Pyridin‐2‐yl)phenol‐Based Four‐Coordinate Organoboron Complexes

“…[ 8 ] More recently, we disclosed an innovative construction of polyaryl N , O ‐bidentate ligands via the merge of ring deconstruction with cycloaromatization of indolizines and cyclopropenones. [ 9 ] We envisioned that the coordination of the in situ assembled polyaryl N , O ‐bidentate ligands and boric acids might be able to produce the fluorescent four‐coordinate organoboron complexes. Herein, we synthesized various polyaryl 2‐(pyridin‐2‐yl)phenol‐based four‐coordinate organoboron complexes from indolizines, [ 10‐11 ] cyclopropenones, [ 12 ] and boric acids (Scheme 1c).…”

Switchable Synthesis of Spirodihydroindolizines and Indolizines from Aurones and Pyridin-2-yl Active Methylene Compounds

“…Indolizines are also an important class of N -containing heterocycles, occurring widely in natural products, synthetic drugs, fluorescent materials, and solar cell sensitizers . Meanwhile, indolizines are versatile synthons for building other functionalized molecules . Accordingly, considerable efforts have been devoted to the synthesis of these heterocyclic motifs .…”