Heck‐Type Cyclization of Oxime Ethers: Stereoselective Carbon–Carbon Bond Formation with Aryl Halides To Produce Heterocyclic Oximes

Transition Metal‐Catalyzed Reactions Involving Oximes

“…In 2007, Ohno and Tanaka et al. for the first time reported a palladium‐catalyzed intramolecular Heck‐type reaction of aryl halides with oxime ethers . The cyclization of O ‐methyl or O ‐benzyl oximes bearing a halogenated aryl group led to indolin‐3‐one derivatives in good yields and high stereoselectivity (Scheme ).…”

Oxime ethers as versatile precursors in organic synthesis: a review

“…102 Heck cyclization of oxime ethers is a well-known reaction and has been the subject of some papers. 103,104 The authors extended their methodology to the direct arylation of oxime ethers, using arenes instead of aryl iodides. 105 Treatment of aromatic aldoxime ethers 112 and arenes 113 with Pd(OAc) 2 (20 mol%) and K 2 S 2 O 8 in TFA at 120 C afforded uorenone oxime ethers 114 in good yields.…”

Synthesis of Fluorenones from Aromatic Aldoxime Ethers and Aryl Halides by Palladium‐Catalyzed Dual CH Activation and Heck Cyclization

“…In 2004, Stoltz and co‐workers reported a palladium‐catalyzed synthesis of functionalized benzofurans and dihydrobenzofurans by direct intramolecular oxidative Heck cyclization of allyl phenyl ether 8. Recently, Tanaka and co‐workers developed a palladium‐catalyzed Heck‐type cyclization of oxime ethers that leads to the formation of 3‐indolinone derivatives 9. In this context, an intermolecular version of Heck cyclization reactions of carbon–nitrogen double bonds is extremely limited.…”