Norbornene-mediated palladium-catalyzed synthesis of fused aromatic carbocycles and heterocycles /by Dino Alberico.
Published: 2006
Language: eng
Number of pages: 374
ISBN-13: 9780494157459
Description: Chapter 2 examines a sequence in which two alkyl-aryl bonds and one alkenyl/aryl bond are formed in one pot. The reaction conditions were optimized and the scope was examined. A variety of symmetrical and unsymmetrical tricyclic heterocycles were synthesized in good yields from a Heck acceptor and an aryl iodide containing two tethered alkyl bromides. This methodology was applied to the synthesis of a tricyclic mescaline analogue.We have developed a norbornene-mediated palladium-catalyzed tandem reaction for the preparation of fused aromatic carbocycles and heterocycles. Chapter 1 describes an alkylation/alkenylation sequence using aryl iodides and bromoenoates. The effect of substitution on the bromoenoate was evaluated. A wide variety of carbon-, oxygen-, and nitrogen-containing functional groups are tolerated allowing for rapid access to highly functionalized aromatic carbocycles.Chapter 3 describes an alkylation/C-H functionalization sequence. In this highly efficient approach, an alkyl-aryl bond and an aryl-heteroaryl bond are created from two C-H bonds in a one-pot process. A wide range of functionalized annulated indoles were synthesized in a convergent manner in high yields.
Notes: Source: Dissertation Abstracts International, Volume: 67-06, Section: B, page: 3133.

Advisor: Mark Lautens

Thesis (Ph.D.)--University of Toronto, 2006.

Includes bibliographic references.

Electronic version licensed for access by U. of T. users.