Regiospecific palladium catalysed tandem cyclisation-anion capture processes. Stereospecific group transfer from organozinc and organoboron reagents

Synthesis and Structure–Activity Relationships of Constrained Heterocyclic Analogues of Combretastatin A4

“…One of the more reliable synthetic pathways is the Heck carbocyclization/ Suzuki-Miyaura coupling protocol (Path A) that uses alkynetethered halogenated arenes and boronic acids as coupling partners. [18] More recently, compounds with an oxindole moiety were successfully prepared by a sequence of carbopalladation, CÀH activation, and CÀC bond formation, from anilides and aryl iodides as the starting materials (Path B). [19] We therefore decided to investigate the preparation of heterocyclic CA4 analogues containing a stereochemically defined substituted exocyclic alkene, by using these palladium-catalyzed domino processes.…”

Synthesis of 3,3‐Disubstituted Oxindoles Containing a 3‐(4‐Aminobut‐2‐ynyl) Unit via Domino Heck–Sonogashira Reaction in Water

“…The domino Heck reaction of 2‐haloaniline derivatives is a very direct, effective method for synthesizing oxindoles. Grigg7a and Somfai6a have employed domino Heck–Suzuki coupling reactions for synthesizing 3,3‐disubstituted oxindoles. In 2007, Zhu and co‐workers13 have developed a domino Heck‐cyanation process for obtaining 3,3‐disubstituted oxindoles with the CN group.…”

Transition‐Metal‐Mediated Routes to 3,3‐Disubstituted Oxindoles through Anilide Cyclisation

“…Treatment of the cyclisation precursor 37b with a variety of boronic acids in the presence of Pd(OAc) 2 , PPh 3 and aqueous Na 2 CO 3 , for example, gave the oxindoles 39 in excellent yields (Table 2). [41] It was crucial to heat the reaction mixtures to 110°C, because direct coupling of the aryl halides with the boronic acids was observed at lower temperatures. The use of a variety of organotin reagents in a similar process is shown in Table 3.…”