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Keywords:

  • biaryls;
  • C[BOND]H activation;
  • cross-coupling;
  • Grignard reagent;
  • iron

Abstract

Direct arylation of the ortho-C[BOND]H bond of an aryl pyridine or an aryl imine with an aryl Grignard reagent has been achieved by using an iron-diamine catalyst and a dichloroalkane as an oxidant in a short reaction time (e.g., 5 min) under mild conditions (0 °C). The use of an aromatic co-solvent, such as chlorobenzene and benzene, and slow addition of the Grignard reagent are essential for the high efficiency of the reaction. The present arylation reaction has distinct merits over the previously developed reaction that used an arylzinc reagent, such as its reaction rate and atom economy. Selective C[BOND]H bond activation occurs in the presence of a leaving group, such as a tosyloxy, chloro, and bromo group. Studies on a stoichiometric reaction and kinetic isotope effects shed light on the reaction intermediate and the C[BOND]H bond-activation step.

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Featured Compounds

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  1. 1 - 44
Compound 1g
Molecular Weight:179.2173
Molecular Formula:C13H9N
InChIKey:WZJYKHNJTSNBHV-UHFFFAOYSA-N
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Compound 2g
Molecular Weight:255.3132
Molecular Formula:C19H13N
InChIKey:HPQOKSZVLDOSQJ-UHFFFAOYSA-N
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Compound 1a
Molecular Weight:155.1959
Molecular Formula:C11H9N
InChIKey:VQGHOUODWALEFC-UHFFFAOYSA-N
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Compound 2a
Molecular Weight:231.2918
Molecular Formula:C17H13N
InChIKey:KHEJPTNZSLUBNF-UHFFFAOYSA-N
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Compound 3a
Molecular Weight:307.3878
Molecular Formula:C23H17N
InChIKey:GYTSRURYVAEJMQ-UHFFFAOYSA-N
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Compound 2h
Molecular Weight:285.3392
Molecular Formula:C20H15NO
InChIKey:QWZBTLHKAPIXKM-UHFFFAOYSA-N
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Compound 1b
Molecular Weight:169.2224
Molecular Formula:C12H11N
InChIKey:JMTCQDNRTSGBGC-UHFFFAOYSA-N
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Compound 1c
Molecular Weight:185.2218
Molecular Formula:C12H11NO
InChIKey:SDVYSLSOAMJTPL-UHFFFAOYSA-N
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Compound 1d
Molecular Weight:198.2637
Molecular Formula:C13H14N2
InChIKey:LWDLQPHZMSWCLF-UHFFFAOYSA-N
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Compound 1e
Molecular Weight:189.641
Molecular Formula:C11H8ClN
InChIKey:BMGXTZHPKNTDHN-UHFFFAOYSA-N
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Compound 1f
Molecular Weight:173.1863
Molecular Formula:C11H8FN
InChIKey:MFVNFXJHJBHQIS-UHFFFAOYSA-N
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Compound 2f
Molecular Weight:249.2823
Molecular Formula:C17H12FN
InChIKey:OQRHCOHVONWKDR-UHFFFAOYSA-N
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Compound 1j
Molecular Weight:161.224
Molecular Formula:C9H7NS
InChIKey:QLPKTAFPRRIFQX-UHFFFAOYSA-N
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Compound 1k
Molecular Weight:194.2319
Molecular Formula:C13H10N2
InChIKey:VSKZGHVPGOMFAV-UHFFFAOYSA-N
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Compound 1h
Molecular Weight:231.2918
Molecular Formula:C17H13N
InChIKey:KHEJPTNZSLUBNF-UHFFFAOYSA-N
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Compound 1i
Molecular Weight:169.2224
Molecular Formula:C12H11N
InChIKey:GRTWYIODJKVPEV-UHFFFAOYSA-N
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Compound 2b
Molecular Weight:245.3184
Molecular Formula:C18H15N
InChIKey:KWLZZXRFPNHSAQ-UHFFFAOYSA-N
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Compound 2c
Molecular Weight:261.3178
Molecular Formula:C18H15NO
InChIKey:XULHGCKUCUENOK-UHFFFAOYSA-N
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Compound 2d
Molecular Weight:274.3596
Molecular Formula:C19H18N2
InChIKey:RXLQRNXFQMWNPN-UHFFFAOYSA-N
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Compound 2e
Molecular Weight:265.737
Molecular Formula:C17H12ClN
InChIKey:GZMOBUHNXVHJAX-UHFFFAOYSA-N
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Compound 2i
Molecular Weight:307.3878
Molecular Formula:C23H17N
InChIKey:GYTSRURYVAEJMQ-UHFFFAOYSA-N
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Compound 2j
Molecular Weight:245.3184
Molecular Formula:C18H15N
InChIKey:BIBHOVYJSQDOJX-UHFFFAOYSA-N
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Compound 2k
Molecular Weight:291.3438
Molecular Formula:C19H17NO2
InChIKey:MCQUDGNKBAJPIT-UHFFFAOYSA-N
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Compound 2l
Molecular Weight:317.4241
Molecular Formula:C22H23NO
InChIKey:XTZLTXHQZZTXMF-UHFFFAOYSA-N
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Compound 2m
Molecular Weight:279.3083
Molecular Formula:C18H14FNO
InChIKey:JGXZWKQOEHQRMN-UHFFFAOYSA-N
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Compound 2n
Molecular Weight:311.3765
Molecular Formula:C22H17NO
InChIKey:CDIBFNQVGIVTJR-UHFFFAOYSA-N
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Compound 2o
Molecular Weight:237.32
Molecular Formula:C15H11NS
InChIKey:IUVAHQDDOGDCBK-UHFFFAOYSA-N
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Compound 2p
Molecular Weight:270.3279
Molecular Formula:C19H14N2
InChIKey:GNDVOWLVNORGSZ-UHFFFAOYSA-N
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Compound 1l
Molecular Weight:239.3123
Molecular Formula:C16H17NO
InChIKey:FAJTVANROHKGST-WUKNDPDISA-N
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Compound 1m
Molecular Weight:251.323
Molecular Formula:C17H17NO
InChIKey:DAHVQOFAMVMRDX-ISLYRVAYSA-N
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Compound 2q
Molecular Weight:210.2711
Molecular Formula:C15H14O
InChIKey:NCSYADOGPPUQKI-UHFFFAOYSA-N
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Compound 2t
Molecular Weight:222.2818
Molecular Formula:C16H14O
InChIKey:ZNPPRZCOXXBMMQ-UHFFFAOYSA-N
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Compound 2r
Molecular Weight:286.367
Molecular Formula:C21H18O
InChIKey:UAYVFBSNNMRSNF-UHFFFAOYSA-N
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Compound 2s
Molecular Weight:268.3502
Molecular Formula:C18H20O2
InChIKey:SNZQYVTXNJPNOX-UHFFFAOYSA-N
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Compound 2u
Molecular Weight:366.43
Molecular Formula:C21H18O4S
InChIKey:MHIBODLLKCHCKP-UHFFFAOYSA-N
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Compound 2v
Molecular Weight:230.69
Molecular Formula:C14H11ClO
InChIKey:QRIDXNVNOVVCSG-UHFFFAOYSA-N
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Compound 2w
Molecular Weight:275.141
Molecular Formula:C14H11BrO
InChIKey:IGFJCZHJYPTBOU-UHFFFAOYSA-N
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Compound 1n
Molecular Weight:395.471
Molecular Formula:C22H21NO4S
InChIKey:YFDOVTTWEXKRPF-HAVVHWLPSA-N
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Compound 1o
Molecular Weight:259.731
Molecular Formula:C15H14ClNO
InChIKey:GTDZYKGDWXSAPU-GZTJUZNOSA-N
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Compound 1p
Molecular Weight:304.182
Molecular Formula:C15H14BrNO
InChIKey:ZOMFVZRAFJIKSY-GZTJUZNOSA-N
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Compound [D]-1a
Molecular Weight:156.202
Molecular Formula:C11H9N
InChIKey:Not Available
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Compound [D5]-1a
Molecular Weight:160.2267
Molecular Formula:C11H9N
InChIKey:Not Available
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Compound [D]-2a
Molecular Weight:232.298
Molecular Formula:C17H13N
InChIKey:Not Available
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Compound [D4]-2a
Molecular Weight:235.3165
Molecular Formula:C17H13N
InChIKey:Not Available
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  1. 1 - 44