Gold-Catalyzed One-Pot Synthesis of 1,3-Disubstituted Allenes from Benzaldehydes and Terminal Alkynes

Danilo M. Lustosa; Simon Clemens; Matthias Rudolph; A. Stephen K. Hashmi

doi:10.1002/adsc.201900824

Gold-Catalyzed One-Pot Synthesis of 1,3-Disubstituted Allenes from Benzaldehydes and Terminal Alkynes

Danilo M. Lustosa, Simon Clemens, Matthias Rudolph, A. Stephen K. Hashmi

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

15 Scopus citations

Abstract

A new and facile one-pot synthesis of 1,3-disubstituted allenes, using cheap and readily available terminal alkynes, benzaldehyde derivatives and morpholine, was developed. A small library of 20 allenes demonstrates a broad applicability, with yields up to 86%. Isotopic-labelling and cross-over experiments strongly indicate that our reaction proceeds via a two-step A³-coupling followed by a 1,5-hydrogen shift process. (Figure presented.).

Original language	English
Pages (from-to)	5050-5056
Number of pages	7
Journal	Advanced Synthesis and Catalysis
Volume	361
Issue number	21
DOIs	https://doi.org/10.1002/adsc.201900824
State	Published - 5 Nov 2019
Externally published	Yes

Keywords

Aldehydes
Alkynes
Deuterium
Gold
Reaction mechanisms

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Access to Document

10.1002/adsc.201900824

Cite this

@article{a0a7bc8340b341d69d0f10dc7b93b9b1,

title = "Gold-Catalyzed One-Pot Synthesis of 1,3-Disubstituted Allenes from Benzaldehydes and Terminal Alkynes",

abstract = "A new and facile one-pot synthesis of 1,3-disubstituted allenes, using cheap and readily available terminal alkynes, benzaldehyde derivatives and morpholine, was developed. A small library of 20 allenes demonstrates a broad applicability, with yields up to 86%. Isotopic-labelling and cross-over experiments strongly indicate that our reaction proceeds via a two-step A3-coupling followed by a 1,5-hydrogen shift process. (Figure presented.).",

keywords = "Aldehydes, Alkynes, Deuterium, Gold, Reaction mechanisms",

author = "Lustosa, {Danilo M.} and Simon Clemens and Matthias Rudolph and Hashmi, {A. Stephen K.}",

note = "Publisher Copyright: {\textcopyright} 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.",

year = "2019",

month = nov,

day = "5",

doi = "10.1002/adsc.201900824",

language = "English",

volume = "361",

pages = "5050--5056",

journal = "Advanced Synthesis and Catalysis",

issn = "1615-4150",

publisher = "Wiley-VCH Verlag",

number = "21",

}

TY - JOUR

T1 - Gold-Catalyzed One-Pot Synthesis of 1,3-Disubstituted Allenes from Benzaldehydes and Terminal Alkynes

AU - Lustosa, Danilo M.

AU - Clemens, Simon

AU - Rudolph, Matthias

AU - Hashmi, A. Stephen K.

PY - 2019/11/5

Y1 - 2019/11/5

N2 - A new and facile one-pot synthesis of 1,3-disubstituted allenes, using cheap and readily available terminal alkynes, benzaldehyde derivatives and morpholine, was developed. A small library of 20 allenes demonstrates a broad applicability, with yields up to 86%. Isotopic-labelling and cross-over experiments strongly indicate that our reaction proceeds via a two-step A3-coupling followed by a 1,5-hydrogen shift process. (Figure presented.).

AB - A new and facile one-pot synthesis of 1,3-disubstituted allenes, using cheap and readily available terminal alkynes, benzaldehyde derivatives and morpholine, was developed. A small library of 20 allenes demonstrates a broad applicability, with yields up to 86%. Isotopic-labelling and cross-over experiments strongly indicate that our reaction proceeds via a two-step A3-coupling followed by a 1,5-hydrogen shift process. (Figure presented.).

KW - Aldehydes

KW - Alkynes

KW - Deuterium

KW - Gold

KW - Reaction mechanisms

UR - http://www.scopus.com/inward/record.url?scp=85073995433&partnerID=8YFLogxK

U2 - 10.1002/adsc.201900824

DO - 10.1002/adsc.201900824

M3 - Article

AN - SCOPUS:85073995433

SN - 1615-4150

VL - 361

SP - 5050

EP - 5056

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 21

ER -

Gold-Catalyzed One-Pot Synthesis of 1,3-Disubstituted Allenes from Benzaldehydes and Terminal Alkynes

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this