Direct access to benzo[b]fluorenes via a gold-catalysed A3-coupling strategy. Issue 10 (5th April 2019)

• Record Type: Journal Article
• Authors: Lustosa, Danilo M.; Cieslik, Patrick; Hartmann, Deborah; Bruckhoff, Tim; Rudolph, Matthias; Rominger, Frank; Hashmi, A. Stephen K.
• Is Part Of: Organic chemistry frontiers. Volume 6:Issue 10(2019)
• Page Start: 1655
• Page End: 1662
• Publication Date: 2019-04-05
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c9qo00260j
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : A one-pot combination of gold catalysis and thermal cyclization provides a fast convergent route to benzo[ b ]fluorenes. Abstract : A one-pot atom- and step-economical method for the synthesis of benzo[ b ]fluorenes, from aldehydes, alkynes and amines, proceeding via an A 3 -coupling/formal [4 + 2] thermal cyclization is described. The transformation generates water as the only by-product and three new carbon–carbon bonds are simultaneously formed. The scope was demonstrated by the synthesis of 32 benzo[ b ]fluorenes and, by specific designing of starting materials, regiocontrol could be accessed for some substrates.