Cobalt-Catalyzed N-O and C-C Bond Cleavage in 1,2-Oxazetidines: Solvent-Controlled C-H Aminomethylation and Hydroxymethylation of Heteroarenes

Song Li; Pengfei Shi; Rui Hua Liu; Xu Hong Hu; Teck Peng Loh

doi:10.1021/acs.orglett.9b00141

Cobalt-Catalyzed N-O and C-C Bond Cleavage in 1,2-Oxazetidines: Solvent-Controlled C-H Aminomethylation and Hydroxymethylation of Heteroarenes

Song Li, Pengfei Shi, Rui Hua Liu, Xu Hong Hu, Teck Peng Loh

School of Chemistry and Moleculai Engineering

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

37 Scopus citations

Abstract

An efficient cobalt-catalyzed ring-opening reaction of bench-stable 1,2-oxazetidines with heteroarenes was unprecedentedly developed. The sustainable Cp∗Co(III) catalyst enables a distinctive merger of C-H activation with concomitant N-O and C-C cleavages of 1,2-oxazetidine, leading to site-selective C-H aminomethylation and hydroxymethylation of heteroaromatic compounds containing a broad range of functional groups. Preliminary control experiments unravel some essential mechanistic features of this one-pot transformation.

Original language	English
Pages (from-to)	1602-1606
Number of pages	5
Journal	Organic Letters
Volume	21
Issue number	6
DOIs	https://doi.org/10.1021/acs.orglett.9b00141
State	Published - 15 Mar 2019

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title = "Cobalt-Catalyzed N-O and C-C Bond Cleavage in 1,2-Oxazetidines: Solvent-Controlled C-H Aminomethylation and Hydroxymethylation of Heteroarenes",

abstract = "An efficient cobalt-catalyzed ring-opening reaction of bench-stable 1,2-oxazetidines with heteroarenes was unprecedentedly developed. The sustainable Cp∗Co(III) catalyst enables a distinctive merger of C-H activation with concomitant N-O and C-C cleavages of 1,2-oxazetidine, leading to site-selective C-H aminomethylation and hydroxymethylation of heteroaromatic compounds containing a broad range of functional groups. Preliminary control experiments unravel some essential mechanistic features of this one-pot transformation.",

author = "Song Li and Pengfei Shi and Liu, {Rui Hua} and Hu, {Xu Hong} and Loh, {Teck Peng}",

note = "Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

year = "2019",

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doi = "10.1021/acs.orglett.9b00141",

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T1 - Cobalt-Catalyzed N-O and C-C Bond Cleavage in 1,2-Oxazetidines

T2 - Solvent-Controlled C-H Aminomethylation and Hydroxymethylation of Heteroarenes

AU - Li, Song

AU - Shi, Pengfei

AU - Liu, Rui Hua

AU - Hu, Xu Hong

AU - Loh, Teck Peng

PY - 2019/3/15

Y1 - 2019/3/15

N2 - An efficient cobalt-catalyzed ring-opening reaction of bench-stable 1,2-oxazetidines with heteroarenes was unprecedentedly developed. The sustainable Cp∗Co(III) catalyst enables a distinctive merger of C-H activation with concomitant N-O and C-C cleavages of 1,2-oxazetidine, leading to site-selective C-H aminomethylation and hydroxymethylation of heteroaromatic compounds containing a broad range of functional groups. Preliminary control experiments unravel some essential mechanistic features of this one-pot transformation.

AB - An efficient cobalt-catalyzed ring-opening reaction of bench-stable 1,2-oxazetidines with heteroarenes was unprecedentedly developed. The sustainable Cp∗Co(III) catalyst enables a distinctive merger of C-H activation with concomitant N-O and C-C cleavages of 1,2-oxazetidine, leading to site-selective C-H aminomethylation and hydroxymethylation of heteroaromatic compounds containing a broad range of functional groups. Preliminary control experiments unravel some essential mechanistic features of this one-pot transformation.

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DO - 10.1021/acs.orglett.9b00141

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SN - 1523-7060

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SP - 1602

EP - 1606

JO - Organic Letters

JF - Organic Letters

IS - 6

ER -

Cobalt-Catalyzed N-O and C-C Bond Cleavage in 1,2-Oxazetidines: Solvent-Controlled C-H Aminomethylation and Hydroxymethylation of Heteroarenes

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