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

14 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

Access to Document

10.1039/c9qo00260j

Cite this

@article{960e7c48aac24a3283ffa5ddbadbe310,

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.\}",

note = "Publisher Copyright: {\textcopyright} 2019 the Partner Organisations.",

year = "2019",

month = may,

day = "21",

doi = "10.1039/c9qo00260j",

language = "English",

volume = "6",

pages = "1655--1662",

journal = "Organic Chemistry Frontiers",

issn = "2052-4110",

publisher = "Royal Society of Chemistry",

number = "10",

}

TY - JOUR

T1 - Direct access to benzo[

T2 - B] fluorenes via a gold-catalysed A3-coupling strategy

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.

UR - https://www.scopus.com/pages/publications/85065822415

U2 - 10.1039/c9qo00260j

DO - 10.1039/c9qo00260j

M3 - Article

AN - SCOPUS:85065822415

SN - 2052-4110

VL - 6

SP - 1655

EP - 1662

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

IS - 10

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this