Cross-dehydrogenative annelation of arynes with C(sp2)–H/N–H or C(sp2)–H/O–H frameworks under Pd or Cu catalysis

Palladium Catalysis: Dependence of the Efficiency of C−C Bond Formation on Carboxylate Ligand and Alkali Metal Carboxylate or Carboxylic Acid Additive. Part C: The Domino Diarylation and Annelation Reactions

“…Treatment of o ‐silylaryl triflates with a fluoride source is an effective procedure for the in‐situ production of arynes, [47] which are highly reactive species used, among others, in palladium catalysis [48] . Thus, Tao and He reacted 1‐iodo‐2‐((2‐methylallyl)oxy)benzene 14 a with o ‐(trimethylsilyl)phenyl triflate in the presence of cesium fluoride, base and Pd 0 catalyst (Scheme 14a) [49] .…”

“…Treatment of o-silylaryl triflates with a fluoride source is an effective procedure for the in-situ production of arynes, [47] which are highly reactive species used, among others, in palladium catalysis. [48] Thus, Tao and He reacted 1-iodo-2-((2methylallyl)oxy)benzene 14 a with o-(trimethylsilyl)phenyl triflate in the presence of cesium fluoride, base and Pd 0 catalyst (Scheme 14a). [49] Annelation product 14a1 was produced in yield strongly depending on the base, as specially exemplified with alkali carboxylates: switching from NaOAc or NEt 3 to CsOCOt-Bu improved the yield from 8 to 94%.…”

Palladium Catalysis: Dependence of the Efficiency of C−C Bond Formation on Carboxylate Ligand and Alkali Metal Carboxylate or Carboxylic Acid Additive. Part B: The Hydro(hetero)arylation, Hydroalkenylation and Hydroalkylation Reactions

“…Treatment of o-silylaryl triflates with a fluoride source is an effective procedure for the in-situ production of arynes, [27] which are highly reactive species used, among others, in palladium catalysis. [28] Thus, Sunnam and Belani synthesized 6a1 from the Pd(OAc) 2catalyzed ortho-phenylation of 2-methoxy-N-(quinolin-8-yl)benzamide using o-(trimethylsilyl)phenyl triflate, potassium fluoride and benzoquinone in increased yield in the presence of carboxylic acid or alkali carboxylate, notably t-BuCO 2 Na (Scheme 6a). [29].…”

Highly selective Cu2+ detection with a naphthalimide-functionalised pillar[5]arene fluorescent chemosensor

“…47 Recent advancements in the effective synthesis and derivatisation of RD-P [5]s, [49][50][51][52][53] contributed by one of us, have successfully made them more widely accessible as novel macrocyclic building blocks for molecular and supramolecular architectures. [54][55][56][57][58][59] Herein, we employed a penta-propargyl modified RD-P [5] 4 (vide infra) as the key precursor for synthesising chemosensors through CuAAC click reactions with azide-functionalised 1,8-naphthalimide fluorophores. 53 The combination of the RD-P [5] scaffold and the classic naphthalimide dye [60][61][62][63][64][65] resulted in the ratiometric fluorescent chemosensor 1 for Cu 2+ ions.…”