RhII-Catalyzed β-C(sp2)-H Alkylation of Enol Ethers, Enamides and Enecarbamates with α-Diazo Dicarbonyl Compounds

被引：9

作者：

McLarney, Brett D. ^{[1
]}

Cavitt, Marchello A. ^{[1
]}

Donnell, Theodore M. ^{[1
]}

Musaev, Djamaladdin G. ^{[3
]}

France, Stefan ^{[1
,2
]}

机构：

[1] Georgia Inst Technol, Sch Chem & Biochem, Atlanta, GA 30332 USA

[2] Georgia Inst Technol, Petit Inst Bioengn & Biosci, Atlanta, GA 30332 USA

[3] Emory Univ, Cherry L Emerson Ctr Sci Computat, Atlanta, GA 30332 USA

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2017年 / 23卷 / 05期

基金：

美国国家科学基金会;

关键词：

addition/elimination; alkylation; C-H activation; diazo compounds; rhodium; EFFECTIVE CORE POTENTIALS; DIMETHYL DIAZOMALONATE; MOLECULAR CALCULATIONS; REACTION COORDINATE; ENAMINES; FUNCTIONALIZATION; ARYLDIAZOACETATES; DIHYDROFURANS; REARRANGEMENT; HYBRIDIZATION;

D O I：

10.1002/chem.201604518

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A Rh-II-catalyzed method for intermolecular alkylation of the beta-C(sp(2))-H bond of enol ethers, enamides, and enecarbamates with alpha-diazo-1,3-dicarbonyl compounds is reported. The products are formed in up to 99% yield and can be readily derivatized under a variety of conditions. By utilizing a combination of experimental and computational studies, the presumptive addition-elimination reaction mechanism was investigated and found to proceed under thermodynamic control at higher temperature. The acquired fundamental knowledge was translated into a strategic reaction design and yielded the first example of the beta-C-H functionalizations of acyclic enol ethers using a-diazo-1,3-dicarbonyl compounds.

引用

页码：1129 / 1135

页数：7

共 50 条

[1] Iron catalyzed β-C(sp2)-H alkylation of enamides
Bertho, Sylvain
Maazaoui, Radhouan
Torun, Damla
Dondasse, Ismael
Abderrahim, Raoudha
Nicolas, Cyril
Gillaizeau, Isabelle
NEW JOURNAL OF CHEMISTRY, 2021, 45 (37) : 17475 - 17482
[2] Rh(II) catalyzed C(sp2)-H alkylation of enol ethers and enamides: Furnishing β,γ-unsaturated 1,3-dicarbonyls
McLarney, Brett
Cavitt, Marchello
Donnell, Theodore
Musaev, Jamal
France, Stefan
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
[3] RhII-Catalyzed Intermolecular C-H Arylation of Aromatics with Diazo Quinones
Wu, Kai
Cao, Bei
Zhou, Cong-Ying
Che, Chi-Ming
CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (19) : 4815 - 4819
[4] β-C(sp2)-H alkylation of enamides using xanthate chemistry
Bertho, Sylvain
Dondasse, Ismael
Retailleau, Pascal
Nicolas, Cyril
Gillaizeau, Isabelle
NEW JOURNAL OF CHEMISTRY, 2020, 44 (17) : 7129 - 7141
[5] MnO2-Catalyzed Oxidative Alkylation of Enamides with Ethers via C(sp3)-H/C(sp2)-H Cross-Dehydrogenative Coupling and Hydrolysis Sequence
Hu, Zhiyan
Tang, Yucai
Zhang, Shan
Li, Xiaoqing
Du, Xiaohua
Xu, Xiangsheng
SYNLETT, 2015, 26 (18) : 2557 - 2560
[6] Rhodium(III)-Catalyzed Switchable β-C(sp2)-H Alkenylation and Alkylation of Acyclic Enamides with Allyl Alcohols
Li, Xiaolan
Liu, Jie
Song, Ruixin
Luo, Xuzhong
Luo, Haiqing
ORGANIC LETTERS, 2024, 26 (17) : 3673 - 3678
[7] Stereoselective Iron-Catalyzed Alkylation of Enamides with Cyclopropanols via Oxidative C(sp2)-H Functionalization
Zhang, Xing
Yang, Tian-Ming
Hu, Lu-Min
Hu, Xu-Hong
ORGANIC LETTERS, 2022, 24 (47) : 8677 - 8682
[8] Development of Transition-Metal-Catalyzed C(sp2)-H Functionalization of Arenes with Diazo Compounds
Liu, Lu
Zhang, Junliang
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2017, 37 (05) : 1117 - 1126
[9] Gold(I)-Catalyzed Hydroxy Group Assisted C(sp2)-H Alkylation of Enaminones with Diazo Compounds To Access 3-Alkyl Chromones
Bagle, Pradip N.
Mane, Manoj V.
Sancheti, Shashank P.
Gade, Amol B.
Shaikh, Samir R.
Baik, Mu-Hyun
Patil, Nitin T.
ORGANIC LETTERS, 2019, 21 (01) : 335 - 339
[10] Organophotoelectrocatalytic C(sp2)-H alkylation of heteroarenes with unactivated C(sp3)-H compounds
Wan, Qinhui
Wu, Xia-Die
Hou, Zhong-Wei
Ma, Yongmin
Wang, Lei
CHEMICAL COMMUNICATIONS, 2024, 60 (42) : 5502 - 5505

← 1 2 3 4 5 →