Synthesis of Phenacene-Helicene Hybrids by Directed Remote Metalation
Polycyclic aromatic hydrocarbons (PAHs) with six and seven rings were synthesized via directed metalation and cross-coupling of chrysenyl N,N-diethyl carboxamides with o-tolyl and methylnaphthalenyl derivatives. In the presence of competing ortho sites, the site selectivity in iodination of chrysenyl amides by directed ortho metalation (DoM) was influenced by the lithium base. The catalyst ligand bite angle was presumably important in the cross-coupling of sterically hindered bulky PAHs. Subsequent directed remote metalation of biaryls under standard conditions and at elevated temperatures afforded various fused six- and seven-ring PAHs, all in good yields and with fluorescent properties.
Kancherla, Sindhu,J?rgensen, K?re B.
supporting information
p. 11140 - 11153
(2020/11/20)
A concise synthesis of novel naphtho[a]carbazoles and benzo[c]carbazoles
Starting from simple indole precursors the synthesis of naphtho[a]carbazoles and benzo[c]carbazoles is described. Key steps include the use of the Suzuki-Miyaura reaction to afford 2- or 3-aryl substituted indoles, as well as a potassium t-butoxide and light assisted aromatic ring-forming reaction.
Pathak, Rakhi,Nhlapo, Johanna M.,Govender, Sameshnee,Michael, Joseph P.,Van Otterlo, Willem A. L.,De Koning, Charles B.
p. 2820 - 2830
(2007/10/03)
The synthesis of naphtho[a]carbazoles and benzo[c]carbazoles
The synthesis of naphtho[a]carbazoles and benzo[c]carbazoles from indole precursors using a reaction mediated by potassium t-butoxide and light is described. The indole precursors were prepared utilizing Suzuki coupling methodology.
De Koning, Charles B.,Michael, Joseph P.,Nhlapo, Johanna M.,Pathak, Rakhi,Van Otterlo, Willem A. L.
p. 705 - 707
(2007/10/03)
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