Controllable α- Or β-Functionalization of α-Diazoketones with Aromatic Amides via Cobalt-Catalyzed C-H Activation: A Regioselective Approach to Isoindolinones

Murong Xu; Yang Yuan; Ye Wang; Qihai Tao; Chengyu Wang; Yanzhong Li

doi:10.1021/acs.orglett.9b02145

Controllable α- Or β-Functionalization of α-Diazoketones with Aromatic Amides via Cobalt-Catalyzed C-H Activation: A Regioselective Approach to Isoindolinones

Murong Xu
, Yang Yuan
, Ye Wang
, Qihai Tao
, Chengyu Wang^*
, Yanzhong Li

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

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

26 Scopus citations

Abstract

Efficient procedures for the selective α- or β-functionalization of α-diazoketones with aromatic amides were developed by using a cobalt catalyst under ligand-free conditions. Normal α-functionalization of α-diazoketones was achieved via C(sp²)-H bond functionalization of aromatic amides in the presence of Co(acac)₂/TBHP. Interestingly, β-functionalization of α-diazoketones was realized with a Co(OAc)₂/AgOAc catalyst system. Further intramolecular cyclization afforded the desired isoindolinones in good to excellent yields.

Original language	English
Pages (from-to)	6264-6269
Number of pages	6
Journal	Organic Letters
Volume	21
Issue number	16
DOIs	https://doi.org/10.1021/acs.orglett.9b02145
State	Published - 16 Aug 2019

Access to Document

10.1021/acs.orglett.9b02145

Cite this

@article{755f80bcadae4153ba155a36a51ac81e,

title = "Controllable α- Or β-Functionalization of α-Diazoketones with Aromatic Amides via Cobalt-Catalyzed C-H Activation: A Regioselective Approach to Isoindolinones",

abstract = "Efficient procedures for the selective α- or β-functionalization of α-diazoketones with aromatic amides were developed by using a cobalt catalyst under ligand-free conditions. Normal α-functionalization of α-diazoketones was achieved via C(sp2)-H bond functionalization of aromatic amides in the presence of Co(acac)2/TBHP. Interestingly, β-functionalization of α-diazoketones was realized with a Co(OAc)2/AgOAc catalyst system. Further intramolecular cyclization afforded the desired isoindolinones in good to excellent yields.",

author = "Murong Xu and Yang Yuan and Ye Wang and Qihai Tao and Chengyu Wang and Yanzhong Li",

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

year = "2019",

month = aug,

day = "16",

doi = "10.1021/acs.orglett.9b02145",

language = "英语",

volume = "21",

pages = "6264--6269",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "16",

}

TY - JOUR

T1 - Controllable α- Or β-Functionalization of α-Diazoketones with Aromatic Amides via Cobalt-Catalyzed C-H Activation

T2 - A Regioselective Approach to Isoindolinones

AU - Xu, Murong

AU - Yuan, Yang

AU - Wang, Ye

AU - Tao, Qihai

AU - Wang, Chengyu

AU - Li, Yanzhong

PY - 2019/8/16

Y1 - 2019/8/16

N2 - Efficient procedures for the selective α- or β-functionalization of α-diazoketones with aromatic amides were developed by using a cobalt catalyst under ligand-free conditions. Normal α-functionalization of α-diazoketones was achieved via C(sp2)-H bond functionalization of aromatic amides in the presence of Co(acac)2/TBHP. Interestingly, β-functionalization of α-diazoketones was realized with a Co(OAc)2/AgOAc catalyst system. Further intramolecular cyclization afforded the desired isoindolinones in good to excellent yields.

AB - Efficient procedures for the selective α- or β-functionalization of α-diazoketones with aromatic amides were developed by using a cobalt catalyst under ligand-free conditions. Normal α-functionalization of α-diazoketones was achieved via C(sp2)-H bond functionalization of aromatic amides in the presence of Co(acac)2/TBHP. Interestingly, β-functionalization of α-diazoketones was realized with a Co(OAc)2/AgOAc catalyst system. Further intramolecular cyclization afforded the desired isoindolinones in good to excellent yields.

UR - https://www.scopus.com/pages/publications/85070746607

U2 - 10.1021/acs.orglett.9b02145

DO - 10.1021/acs.orglett.9b02145

M3 - 文章

C2 - 31343889

AN - SCOPUS:85070746607

SN - 1523-7060

VL - 21

SP - 6264

EP - 6269

JO - Organic Letters

JF - Organic Letters

IS - 16

ER -

Controllable α- Or β-Functionalization of α-Diazoketones with Aromatic Amides via Cobalt-Catalyzed C-H Activation: A Regioselective Approach to Isoindolinones

Abstract

Access to Document

Other files and links

Fingerprint

Cite this