Pd-Catalyzed Alkyne Insertion/C-H Activation/[4+2] Carboannulation of Alkenes to the Synthesis of Polycyclics

被引：12

作者：

Guo, Songjin ^{[1
,2
]}

Li, Panpan ^{[1
,2
]}

Guan, Zhe ^{[1
,2
]}

Cai, Libo ^{[1
,2
]}

Chen, Siwei ^{[1
,2
]}

Lin, Aijun ^{[1
,2
]}

Yao, Hequan ^{[1
,2
]}

机构：

[1] China Pharmaceut Univ, Sch Pharm, State Key Lab Nat Med, Nanjing 210009, Jiangsu, Peoples R China

[2] China Pharmaceut Univ, Sch Pharm, Dept Med Chem, Nanjing 210009, Jiangsu, Peoples R China

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 04期

基金：

中国国家自然科学基金;

关键词：

INTERNAL ALKYNES; ARYL IODIDES; CYCLOCARBOPALLADATION; FUNCTIONALIZATION; CYCLIZATION; REACTIVITY; PATHWAYS;

D O I：

10.1021/acs.orglett.8b03884

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An unprecedented Pd-catalyzed alkyne insertion/C-H activation/intramolecular [4 + 2] carboannulation of alkenes has been reported. In this transformation, the C-H activation was triggered by an in situ generated alkenylpalladium species via the Pd-catalyzed cross-coupling reaction of aryl iodides and alkynes. Subsequently, the resulting five-membered C, C-palladacyde intermediates were added across the alkenes, providing a unique approach to access diversified polycyclics in good efficiency. Two new rings and three C-C bonds were formed in one pot.

引用

页码：921 / 925

页数：5

共 50 条

[1] Pd-Catalyzed Spirocyclization via C-H Activation and Benzyne Insertion
Yoon, Hyung
Lossouarn, Alexis
Landau, Felicitas
Lautens, Mark
ORGANIC LETTERS, 2016, 18 (24) : 6324 - 6327
[2] Synthesis of cyclopropanes by Pd-catalyzed activation of alkyl C-H bonds
Huang, Qinhua
Larock, Richard C.
TETRAHEDRON LETTERS, 2009, 50 (52) : 7235 - 7238
[3] Synthesis of phenanthridine and phenanthridinone derivatives based on Pd-catalyzed C-H activation
Rafiee, Fatemeh
APPLIED ORGANOMETALLIC CHEMISTRY, 2017, 31 (12)
[4] Cobalt(III)-Catalyzed [4+2] Annulation of Heterobicyclic Alkenes by sp2 C-H Activation
Dey, Arnab
Rathi, Anuja
Volla, Chandra M. R.
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (07) : 1362 - 1367
[5] Vinylic Trifluoromethylselenolation via Pd-Catalyzed C-H Activation
de Zordo-Banliat, Arnaud
Grollier, Kevin
Vigier, Jordan
Jeanneau, Erwann
Dagousset, Guillaume
Pegot, Bruce
Magnier, Emmanuel
Billard, Thierry
CHEMISTRY-A EUROPEAN JOURNAL, 2022, 28 (63)
[6] Musings on the mechanistic manifold of Pd-catalyzed C-H activation
Paton, Robert S.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
[7] Hexafluoroisopropanol: the magical solvent for Pd-catalyzed C-H activation
Bhattacharya, Trisha
Ghosh, Animesh
Maiti, Debabrata
CHEMICAL SCIENCE, 2021, 12 (11) : 3857 - 3870
[8] Rhodium catalyzed C-H activation and hydroamination in a highly selective redox [4+2] imine/alkyne annulation
Manan, Rajith
Zhao, Pinjing
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
[9] Palladium-Catalyzed Synthesis of Dihydrobenzoindolones via C-H Bond Activation and Alkyne Insertion
Rodriguez, Jose F.
Marchese, Austin D.
Lautens, Mark
ORGANIC LETTERS, 2018, 20 (14) : 4367 - 4370
[10] Pd-catalyzed silylation of alkenes via allylic C-H bond functionalization
Zhao, Tony S. N.
Larsson, Johanna M.
Szabo, Kalman J.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244

← 1 2 3 4 5 →