Quaternary Ammonium Salts as Alkylating Reagents in C-H Activation Chemistry

M. Spettel; R. Pollice; M. Schnürch

doi:10.1021/acs.orglett.7b01946

Quaternary Ammonium Salts as Alkylating Reagents in C-H Activation Chemistry

M. Spettel, R. Pollice, M. Schnürch

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

26 Citations (Scopus)

Abstract

A rhodium(I)-catalyzed alkylation reaction of benzylic amines via C(sp3)–H activation using quaternary ammonium salts as alkyl source is described. The reaction proceeds via in situ formation of an olefin via Hofmann elimination, which is the actual alkylating reagent. This represents an operationally simple method for substituting gaseous and liquid olefins with solid quaternary ammonium salts as alkylating reagents, which is transferable to other C–H activation protocols as well.

Original language	English
Pages (from-to)	4287–4290
Number of pages	4
Journal	Organic letters
Volume	19
Issue number	16
DOIs	https://doi.org/10.1021/acs.orglett.7b01946
Publication status	Published - 2017
Externally published	Yes

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title = "Quaternary Ammonium Salts as Alkylating Reagents in C-H Activation Chemistry",

abstract = "A rhodium(I)-catalyzed alkylation reaction of benzylic amines via C(sp3)–H activation using quaternary ammonium salts as alkyl source is described. The reaction proceeds via in situ formation of an olefin via Hofmann elimination, which is the actual alkylating reagent. This represents an operationally simple method for substituting gaseous and liquid olefins with solid quaternary ammonium salts as alkylating reagents, which is transferable to other C–H activation protocols as well.",

author = "M. Spettel and R. Pollice and M. Schn{\"u}rch",

year = "2017",

doi = "10.1021/acs.orglett.7b01946",

language = "English",

volume = "19",

pages = "4287–4290",

journal = "Organic letters",

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T1 - Quaternary Ammonium Salts as Alkylating Reagents in C-H Activation Chemistry

AU - Spettel, M.

AU - Pollice, R.

AU - Schnürch, M.

PY - 2017

Y1 - 2017

N2 - A rhodium(I)-catalyzed alkylation reaction of benzylic amines via C(sp3)–H activation using quaternary ammonium salts as alkyl source is described. The reaction proceeds via in situ formation of an olefin via Hofmann elimination, which is the actual alkylating reagent. This represents an operationally simple method for substituting gaseous and liquid olefins with solid quaternary ammonium salts as alkylating reagents, which is transferable to other C–H activation protocols as well.

AB - A rhodium(I)-catalyzed alkylation reaction of benzylic amines via C(sp3)–H activation using quaternary ammonium salts as alkyl source is described. The reaction proceeds via in situ formation of an olefin via Hofmann elimination, which is the actual alkylating reagent. This represents an operationally simple method for substituting gaseous and liquid olefins with solid quaternary ammonium salts as alkylating reagents, which is transferable to other C–H activation protocols as well.

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U2 - 10.1021/acs.orglett.7b01946

DO - 10.1021/acs.orglett.7b01946

M3 - Article

SN - 1523-7060

VL - 19

SP - 4287

EP - 4290

JO - Organic letters

JF - Organic letters

IS - 16

ER -

Quaternary Ammonium Salts as Alkylating Reagents in C-H Activation Chemistry

Abstract

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