Manganese-Catalyzed C−H Functionalizations: Hydroarylations and Alkenylations Involving an Unexpected Heteroaryl Shift

Chengming Wang; Ai Wang; Magnus Rueping

doi:10.1002/anie.201704682

Manganese-Catalyzed C−H Functionalizations: Hydroarylations and Alkenylations Involving an Unexpected Heteroaryl Shift

Chengming Wang, Ai Wang, Magnus Rueping^*

^*Corresponding author for this work

Physical Sciences and Engineering

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

133 Scopus citations

Abstract

A manganese-catalyzed regio- and stereoselective hydroarylation of allenes is reported. The C−H functionalization method provides access to various alkenylated indoles in excellent yields. Moreover, a hydroarylation/cyclization cascade involving an unexpected C−N bond cleavage and aryl shift has been developed, which provides a new synthetic approach to substituted pyrroloindolones.

Original language	English (US)
Pages (from-to)	9935-9938
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	56
Issue number	33
DOIs	https://doi.org/10.1002/anie.201704682
State	Published - Aug 7 2017

Keywords

allenes
cascade cyclization
hydroarylation
indoles
manganese

ASJC Scopus subject areas

General Chemistry
Catalysis

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10.1002/anie.201704682

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title = "Manganese-Catalyzed C−H Functionalizations: Hydroarylations and Alkenylations Involving an Unexpected Heteroaryl Shift",

abstract = "A manganese-catalyzed regio- and stereoselective hydroarylation of allenes is reported. The C−H functionalization method provides access to various alkenylated indoles in excellent yields. Moreover, a hydroarylation/cyclization cascade involving an unexpected C−N bond cleavage and aryl shift has been developed, which provides a new synthetic approach to substituted pyrroloindolones.",

keywords = "allenes, cascade cyclization, hydroarylation, indoles, manganese",

author = "Chengming Wang and Ai Wang and Magnus Rueping",

note = "Publisher Copyright: {\textcopyright} 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2017",

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T2 - Hydroarylations and Alkenylations Involving an Unexpected Heteroaryl Shift

AU - Wang, Chengming

AU - Wang, Ai

AU - Rueping, Magnus

PY - 2017/8/7

Y1 - 2017/8/7

N2 - A manganese-catalyzed regio- and stereoselective hydroarylation of allenes is reported. The C−H functionalization method provides access to various alkenylated indoles in excellent yields. Moreover, a hydroarylation/cyclization cascade involving an unexpected C−N bond cleavage and aryl shift has been developed, which provides a new synthetic approach to substituted pyrroloindolones.

AB - A manganese-catalyzed regio- and stereoselective hydroarylation of allenes is reported. The C−H functionalization method provides access to various alkenylated indoles in excellent yields. Moreover, a hydroarylation/cyclization cascade involving an unexpected C−N bond cleavage and aryl shift has been developed, which provides a new synthetic approach to substituted pyrroloindolones.

KW - allenes

KW - cascade cyclization

KW - hydroarylation

KW - indoles

KW - manganese

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U2 - 10.1002/anie.201704682

DO - 10.1002/anie.201704682

M3 - Article

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JF - Angewandte Chemie - International Edition

IS - 33

ER -

Manganese-Catalyzed C−H Functionalizations: Hydroarylations and Alkenylations Involving an Unexpected Heteroaryl Shift

Abstract

Keywords

ASJC Scopus subject areas

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