Palladium-Catalyzed Intermolecular Polarity-Mismatched Addition of Unactivated Alkyl Radicals to Unactivated Alkenes

Xiaojin Wu; Guanlin Xiao; Yalan Ding; Ying Zhan; Yao Zhao; Rizhi Chen; Teck Peng Loh

doi:10.1021/acscatal.0c04013

Palladium-Catalyzed Intermolecular Polarity-Mismatched Addition of Unactivated Alkyl Radicals to Unactivated Alkenes

Xiaojin Wu^*, Guanlin Xiao, Yalan Ding, Ying Zhan, Yao Zhao, Rizhi Chen, Teck Peng Loh

^*Corresponding author for this work

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

38 Citations (Scopus)

Abstract

A palladium-catalyzed intermolecular polarity-mismatched addition of unactivated alkyl radicals to unactivated alkenes was developed for the first time. In the two-component dicarbofunctionalization, a variety of primary, secondary, and tertiary unactivated alkyl halides regioselectively reacted with various unactivated olefins. A series of structurally complex heteropolycycles decorated with a quaternary carbon center have been efficiently synthesized.

Original language	English
Pages (from-to)	14107-14116
Number of pages	10
Journal	ACS Catalysis
Volume	10
Issue number	23
DOIs	https://doi.org/10.1021/acscatal.0c04013
Publication status	Published - Dec 4 2020
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2020 American Chemical Society.

ASJC Scopus Subject Areas

Catalysis
General Chemistry

Keywords

heteropolycycles
inert C(sp)-C(sp) bond formation
polarity-mismatched radical addition
reverse cascade addition process
unactivated alkenes

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10.1021/acscatal.0c04013

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title = "Palladium-Catalyzed Intermolecular Polarity-Mismatched Addition of Unactivated Alkyl Radicals to Unactivated Alkenes",

abstract = "A palladium-catalyzed intermolecular polarity-mismatched addition of unactivated alkyl radicals to unactivated alkenes was developed for the first time. In the two-component dicarbofunctionalization, a variety of primary, secondary, and tertiary unactivated alkyl halides regioselectively reacted with various unactivated olefins. A series of structurally complex heteropolycycles decorated with a quaternary carbon center have been efficiently synthesized.",

keywords = "heteropolycycles, inert C(sp)-C(sp) bond formation, polarity-mismatched radical addition, reverse cascade addition process, unactivated alkenes",

author = "Xiaojin Wu and Guanlin Xiao and Yalan Ding and Ying Zhan and Yao Zhao and Rizhi Chen and Loh, \{Teck Peng\}",

note = "Publisher Copyright: {\textcopyright} 2020 American Chemical Society.",

year = "2020",

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doi = "10.1021/acscatal.0c04013",

language = "English",

volume = "10",

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TY - JOUR

T1 - Palladium-Catalyzed Intermolecular Polarity-Mismatched Addition of Unactivated Alkyl Radicals to Unactivated Alkenes

AU - Wu, Xiaojin

AU - Xiao, Guanlin

AU - Ding, Yalan

AU - Zhan, Ying

AU - Zhao, Yao

AU - Chen, Rizhi

AU - Loh, Teck Peng

PY - 2020/12/4

Y1 - 2020/12/4

N2 - A palladium-catalyzed intermolecular polarity-mismatched addition of unactivated alkyl radicals to unactivated alkenes was developed for the first time. In the two-component dicarbofunctionalization, a variety of primary, secondary, and tertiary unactivated alkyl halides regioselectively reacted with various unactivated olefins. A series of structurally complex heteropolycycles decorated with a quaternary carbon center have been efficiently synthesized.

AB - A palladium-catalyzed intermolecular polarity-mismatched addition of unactivated alkyl radicals to unactivated alkenes was developed for the first time. In the two-component dicarbofunctionalization, a variety of primary, secondary, and tertiary unactivated alkyl halides regioselectively reacted with various unactivated olefins. A series of structurally complex heteropolycycles decorated with a quaternary carbon center have been efficiently synthesized.

KW - heteropolycycles

KW - inert C(sp)-C(sp) bond formation

KW - polarity-mismatched radical addition

KW - reverse cascade addition process

KW - unactivated alkenes

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UR - http://www.scopus.com/inward/citedby.url?scp=85096589856&partnerID=8YFLogxK

U2 - 10.1021/acscatal.0c04013

DO - 10.1021/acscatal.0c04013

M3 - Article

AN - SCOPUS:85096589856

SN - 2155-5435

VL - 10

SP - 14107

EP - 14116

JO - ACS Catalysis

JF - ACS Catalysis

IS - 23

ER -

Palladium-Catalyzed Intermolecular Polarity-Mismatched Addition of Unactivated Alkyl Radicals to Unactivated Alkenes

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

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