Organocatalytic C-H activation reactions

Abstract

Organocatalytic C-H activation reactions have recently been developed besides the traditional metal-catalysed C-H activation reactions. The recent non-asymmetric and asymmetric C-H activation reactions mediated by organocatalysts are discussed in this review.

Keywords: C–H activation; asymmetric; non-asymmetric; organocatalysis; organocatalytic.

Scheme 1

Triflic acid-catalysed synthesis of cyclic aminals.

Scheme 2

PTSA-catalysed synthesis of cyclic aminals.

Scheme 3

Plausible mechanism for cyclic aminal synthesis.

Scheme 4

Annulation cascade reaction with double nucleophiles.

Scheme 5

Mechanism for the indole-annulation cascade reaction.

Scheme 6

Synthesis of N-alkylpyrroles and δ-hydroxypyrroles.

Scheme 7

Synthesis of N-alkylindoles 9 and N-alkylindolines 10.

Scheme 8

Mechanistic study for the N-alkylpyrrole formation.

Scheme 9

Benzoic acid catalysed decarboxylative redox amination.

Scheme 10

Organocatalytic redox reaction of ortho-(dialkylamino)cinnamaldehydes.

Scheme 11

Mechanism for aminocatalytic redox reaction of ortho-(dialkylamino)cinnamaldehydes.

Scheme 12

Asymmetric synthesis of tetrahydroquinolines having gem-methyl ester groups.

Scheme 13

Asymmetric synthesis of tetrahydroquinolines from chiral substrates 18.

Scheme 14

Organocatalytic biaryl synthesis by Kwong, Lei and co-workers.

Scheme 15

Organocatalytic biaryl synthesis by Shi and co-workers.

Scheme 16

Organocatalytic biaryl synthesis by Hayashi and co-workers.

Scheme 17

Proposed mechanism for organocatalytic biaryl synthesis.