Benzenoid Ring Functionalization of Indoles and Tryptophols via Combined Directed Ortho Metalation-Cross Coupling Methodology

1995 ◽  
Vol 60 (6) ◽  
pp. 1484-1485 ◽  
Author(s):  
Edward J. Griffen ◽  
David G. Roe ◽  
Victor Snieckus
Keyword(s):  
Cross Coupling ◽  
Ortho Metalation ◽  
Benzenoid Ring

Directed ortho metalation - cross coupling links. Carbamoyl rendition of the baker-venkataraman rearrangement. Regiospecific route to substituted 4-hydroxycoumarins

1998 ◽  
Vol 39 (28) ◽  
pp. 4995-4998 ◽  
Author(s):  
Alexey V. Kalinin ◽  
Alcides J.M. da Silva ◽  
Claudio C. Lopes ◽  
Rosangela S.C. Lopes ◽  
Victor Snieckus
Keyword(s):  
Cross Coupling ◽  
Ortho Metalation

The directed ortho metalation - palladium catalyzed cross coupling connection. A general regiospecific route to 9-phenanthrols and phenanthrenes. Exploratory further metalation

2000 ◽  
Vol 78 (6) ◽  
pp. 905-919 ◽  
Author(s):  
Jian-min Fu ◽  
Victor Snieckus
Keyword(s):  
Cross Coupling ◽  
Ring Contraction ◽  
Ortho Metalation ◽  
Palladium Catalyzed ◽  
General Synthesis

A new general and regiospecific synthesis of 9-phenanthrols (1 +2 [Formula: see text] 3 [Formula: see text] 4, Scheme 1, Table 1) proceeding by a Directed ortho Metalation (DoM), Suzuki-Miyaura cross coupling, and a new LDA-mediated Directed remote Metalation sequence is described. The facile Pd-catalyzed hydrogenolysis of the phenanthrols 4 into the corresponding phenanthrenes 5 via their triflates 18 translates the original DoM regioselectivity also into a general synthesis of phenanthrenes (Table 2). Further DoM (19 [Formula: see text]20, 21; 24 [Formula: see text]25), cross coupling (20c [Formula: see text]23), as well as oxidation - ring contraction (4b, 4f [Formula: see text]28a, 28b) chemistry of phenanthrene derivatives is reported.Key words: 9-phenanthrols, directed ortho metalation, Suzuki cross coupling, synthesis.

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