Aryl-aryl Stille and Suzuki-Miyaura cross-coupling reactions on solid support

The Stille and Suzuki-Miyaura cross coupling reactions in solution phase have proven to be effective methods for the formation of new carbon-carbon bonds. The work contained herein describes the adaptation of these reactions to the solid support.; Chapter 1. The Stille cross coupling reaction on solid support using an ester linker is described. New cleavage condition of the ester linker involving LiOH hydrolysis is reported. Merrifield resin - linked halo benzoates undergo Pd(0) catalysed coupling with a wide range of stannanes to produce after cleavage styryl, biaryl and heterobiaryl carboxylic acids in 71 → 95% isolated yields.; Chapter 2. The synthesis of biaryl and heterobiaryl aldehydes in 45 → 95% yields by Suzuki-Miyaura cross coupling reaction on Merrifield - Leznoff acetal - linked halo benzaldehydes followed by mild acid hydrolysis is reported; synthetic utility for heterocycles based on solution phase Directed ortho Metalation chemistry is demonstrated in two prototype cases. Phenanthridine and 6H-dibenzo[ b,d]pyran-6-one were synthesised in, 90% and 71%, respectively, overall isolated yields.