Co                         I                         -Catalyzed Barbier Reactions of Aromatic Halides with Aromatic Aldehydes and Imines

Marc Presset; Jérôme Paul; Ghania Nait Cherif; Nisanthan Ratnam; Nicolas Laloi; Eric Léonel; Corinne Gosmini; Erwan Le Gall

doi:10.1002/chem.201806239

Co ^I -Catalyzed Barbier Reactions of Aromatic Halides with Aromatic Aldehydes and Imines

Marc Presset
, Jérôme Paul
, Ghania Nait Cherif
, Nisanthan Ratnam
, Nicolas Laloi
, Eric Léonel
, Corinne Gosmini
, Erwan Le Gall

Equipe Electrochimie et Synthèse Organique
Institut de Chimie et des Matériaux de Paris Est, CNRS UPEC/UMR 7182
CNRS

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

40 Citations (Scopus)

Abstract

The reductive Barbier coupling of aromatic halides and electrophiles has been achieved using a CoBr ₂ /1,10-phenanthroline catalytic system and over stoichiometric amounts of zinc. The reaction displayed a broad scope of substrates, including (hetero)aryl chlorides as pro-nucleophiles and aldehydes or imines as electrophiles, leading to diarylmethanols and diarylmethylamines in moderate to excellent yields, respectively.

Original language	English
Pages (from-to)	4491-4495
Number of pages	5
Journal	Chemistry - A European Journal
Volume	25
Issue number	17
DOIs	https://doi.org/10.1002/chem.201806239
Publication status	Published - 21 Mar 2019
Externally published	Yes

Keywords

Barbier
Mannich
cobalt
reductive coupling
zinc

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10.1002/chem.201806239

Cite this

Presset, M., Paul, J., Cherif, G. N., Ratnam, N., Laloi, N., Léonel, E., Gosmini, C., & Le Gall, E. (2019). Co ^I -Catalyzed Barbier Reactions of Aromatic Halides with Aromatic Aldehydes and Imines Chemistry - A European Journal, 25(17), 4491-4495. https://doi.org/10.1002/chem.201806239

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title = " Co I -Catalyzed Barbier Reactions of Aromatic Halides with Aromatic Aldehydes and Imines ",

abstract = " The reductive Barbier coupling of aromatic halides and electrophiles has been achieved using a CoBr 2 /1,10-phenanthroline catalytic system and over stoichiometric amounts of zinc. The reaction displayed a broad scope of substrates, including (hetero)aryl chlorides as pro-nucleophiles and aldehydes or imines as electrophiles, leading to diarylmethanols and diarylmethylamines in moderate to excellent yields, respectively.",

keywords = "Barbier, Mannich, cobalt, reductive coupling, zinc",

author = "Marc Presset and J{\'e}r{\^o}me Paul and Cherif, \{Ghania Nait\} and Nisanthan Ratnam and Nicolas Laloi and Eric L{\'e}onel and Corinne Gosmini and \{Le Gall\}, Erwan",

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

year = "2019",

month = mar,

day = "21",

doi = "10.1002/chem.201806239",

language = "English",

volume = "25",

pages = "4491--4495",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "John Wiley and Sons Inc",

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}

Presset, M, Paul, J, Cherif, GN, Ratnam, N, Laloi, N, Léonel, E, Gosmini, C & Le Gall, E 2019, ' Co ^I -Catalyzed Barbier Reactions of Aromatic Halides with Aromatic Aldehydes and Imines ', Chemistry - A European Journal, vol. 25, no. 17, pp. 4491-4495. https://doi.org/10.1002/chem.201806239

Co ^I -Catalyzed Barbier Reactions of Aromatic Halides with Aromatic Aldehydes and Imines . / Presset, Marc; Paul, Jérôme; Cherif, Ghania Nait et al.
In: Chemistry - A European Journal, Vol. 25, No. 17, 21.03.2019, p. 4491-4495.

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

TY - JOUR

T1 - Co I -Catalyzed Barbier Reactions of Aromatic Halides with Aromatic Aldehydes and Imines

AU - Presset, Marc

AU - Paul, Jérôme

AU - Cherif, Ghania Nait

AU - Ratnam, Nisanthan

AU - Laloi, Nicolas

AU - Léonel, Eric

AU - Gosmini, Corinne

AU - Le Gall, Erwan

PY - 2019/3/21

Y1 - 2019/3/21

N2 - The reductive Barbier coupling of aromatic halides and electrophiles has been achieved using a CoBr 2 /1,10-phenanthroline catalytic system and over stoichiometric amounts of zinc. The reaction displayed a broad scope of substrates, including (hetero)aryl chlorides as pro-nucleophiles and aldehydes or imines as electrophiles, leading to diarylmethanols and diarylmethylamines in moderate to excellent yields, respectively.

AB - The reductive Barbier coupling of aromatic halides and electrophiles has been achieved using a CoBr 2 /1,10-phenanthroline catalytic system and over stoichiometric amounts of zinc. The reaction displayed a broad scope of substrates, including (hetero)aryl chlorides as pro-nucleophiles and aldehydes or imines as electrophiles, leading to diarylmethanols and diarylmethylamines in moderate to excellent yields, respectively.

KW - Barbier

KW - Mannich

KW - cobalt

KW - reductive coupling

KW - zinc

U2 - 10.1002/chem.201806239

DO - 10.1002/chem.201806239

M3 - Article

C2 - 30793810

AN - SCOPUS:85061970471

SN - 0947-6539

VL - 25

SP - 4491

EP - 4495

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 17

ER -

Co I -Catalyzed Barbier Reactions of Aromatic Halides with Aromatic Aldehydes and Imines

Abstract

Keywords

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Co ^I -Catalyzed Barbier Reactions of Aromatic Halides with Aromatic Aldehydes and Imines