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

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

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",

number = "17",

}

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