Direct access to benzo[: B] fluorenes via a gold-catalysed A3-coupling strategy

Danilo M. Lustosa; Patrick Cieslik; Deborah Hartmann; Tim Bruckhoff; Matthias Rudolph; Frank Rominger; A. Stephen K. Hashmi

doi:10.1039/c9qo00260j

Direct access to benzo[: B] fluorenes via a gold-catalysed A³-coupling strategy

Danilo M. Lustosa, Patrick Cieslik, Deborah Hartmann, Tim Bruckhoff, Matthias Rudolph, Frank Rominger, A. Stephen K. Hashmi

Research output: Contribution to journal › Article › peer-review

13 Scopus citations

Abstract

A one-pot atom-and step-economical method for the synthesis of benzo[b]fluorenes, from aldehydes, alkynes and amines, proceeding via an A³-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.

Original language	English
Pages (from-to)	1655-1662
Number of pages	8
Journal	Organic Chemistry Frontiers
Volume	6
Issue number	10
DOIs	https://doi.org/10.1039/c9qo00260j
State	Published - 21 May 2019
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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title = "Direct access to benzo[: B] fluorenes via a gold-catalysed A3-coupling strategy",

abstract = "A one-pot atom-and step-economical method for the synthesis of benzo[b]fluorenes, from aldehydes, alkynes and amines, proceeding via an A3-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.",

author = "Lustosa, {Danilo M.} and Patrick Cieslik and Deborah Hartmann and Tim Bruckhoff and Matthias Rudolph and Frank Rominger and Hashmi, {A. Stephen K.}",

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AU - Lustosa, Danilo M.

AU - Cieslik, Patrick

AU - Hartmann, Deborah

AU - Bruckhoff, Tim

AU - Rudolph, Matthias

AU - Rominger, Frank

AU - Hashmi, A. Stephen K.

PY - 2019/5/21

Y1 - 2019/5/21

N2 - A one-pot atom-and step-economical method for the synthesis of benzo[b]fluorenes, from aldehydes, alkynes and amines, proceeding via an A3-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.

AB - A one-pot atom-and step-economical method for the synthesis of benzo[b]fluorenes, from aldehydes, alkynes and amines, proceeding via an A3-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.

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JO - Organic Chemistry Frontiers

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IS - 10

ER -

Direct access to benzo[: B] fluorenes via a gold-catalysed A³-coupling strategy

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