Photoredox-Mediated Minisci-type Alkylation of N-Heteroarenes with Alkanes with High Methylene Selectivity

Guo Xing Li; Xiafei Hu; Gang He; Gong Chen

doi:10.1021/acscatal.8b04079

Photoredox-Mediated Minisci-type Alkylation of N-Heteroarenes with Alkanes with High Methylene Selectivity

Guo Xing Li, Xiafei Hu, Gang He, Gong Chen

Chemistry

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

90 Scopus citations

Abstract

We report a highly efficient and chemoselective Minisci-type alkylation reaction of N-heteroarenes with alkanes under the reagent control of a hypervalent iodine oxidant PFBI-OH. In addition to the high reactivity, PFBI-OH demonstrated a high steric sensitivity for H abstraction of alkanes. This reaction is selective for more sterically accessible secondary C-H bonds over weaker tertiary C-H bonds. High selectivity toward penultimate methylene groups was observed for a wide range of acyclic alkanes.

Original language	English (US)
Pages (from-to)	11847-11853
Number of pages	7
Journal	ACS Catalysis
Volume	8
Issue number	12
DOIs	https://doi.org/10.1021/acscatal.8b04079
State	Published - Dec 7 2018

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)

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10.1021/acscatal.8b04079

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title = "Photoredox-Mediated Minisci-type Alkylation of N-Heteroarenes with Alkanes with High Methylene Selectivity",

abstract = "We report a highly efficient and chemoselective Minisci-type alkylation reaction of N-heteroarenes with alkanes under the reagent control of a hypervalent iodine oxidant PFBI-OH. In addition to the high reactivity, PFBI-OH demonstrated a high steric sensitivity for H abstraction of alkanes. This reaction is selective for more sterically accessible secondary C-H bonds over weaker tertiary C-H bonds. High selectivity toward penultimate methylene groups was observed for a wide range of acyclic alkanes.",

author = "Li, {Guo Xing} and Xiafei Hu and Gang He and Gong Chen",

note = "Funding Information: We gratefully thank Natural Science Foundation of China (21672105, 21725204, 91753124), Natural Science Foundation of Tianjin (18JCZDJC32800), and Laviana for financial support of this work. This work is dedicated to the 100th anniversary of Nankai University. Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

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doi = "10.1021/acscatal.8b04079",

language = "English (US)",

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T1 - Photoredox-Mediated Minisci-type Alkylation of N-Heteroarenes with Alkanes with High Methylene Selectivity

AU - Li, Guo Xing

AU - Hu, Xiafei

AU - He, Gang

AU - Chen, Gong

N1 - Funding Information: We gratefully thank Natural Science Foundation of China (21672105, 21725204, 91753124), Natural Science Foundation of Tianjin (18JCZDJC32800), and Laviana for financial support of this work. This work is dedicated to the 100th anniversary of Nankai University. Publisher Copyright: © 2018 American Chemical Society.

PY - 2018/12/7

Y1 - 2018/12/7

N2 - We report a highly efficient and chemoselective Minisci-type alkylation reaction of N-heteroarenes with alkanes under the reagent control of a hypervalent iodine oxidant PFBI-OH. In addition to the high reactivity, PFBI-OH demonstrated a high steric sensitivity for H abstraction of alkanes. This reaction is selective for more sterically accessible secondary C-H bonds over weaker tertiary C-H bonds. High selectivity toward penultimate methylene groups was observed for a wide range of acyclic alkanes.

AB - We report a highly efficient and chemoselective Minisci-type alkylation reaction of N-heteroarenes with alkanes under the reagent control of a hypervalent iodine oxidant PFBI-OH. In addition to the high reactivity, PFBI-OH demonstrated a high steric sensitivity for H abstraction of alkanes. This reaction is selective for more sterically accessible secondary C-H bonds over weaker tertiary C-H bonds. High selectivity toward penultimate methylene groups was observed for a wide range of acyclic alkanes.

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JF - ACS Catalysis

IS - 12

ER -

Photoredox-Mediated Minisci-type Alkylation of N-Heteroarenes with Alkanes with High Methylene Selectivity

Abstract

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