Contrasteric coupling of allenes and tetrahydroisoquinolines by iron-catalysed allenic C(sp2)-H functionalisation

被引：7

作者：

Xia, Yue ^{[1
]}

Wade, Nicholas W. ^{[1
]}

Palermo, Philip N. ^{[1
]}

Wang, Yidong ^{[1
]}

Wang, Yi-Ming ^{[1
]}

机构：

[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

来源：

CHEMICAL COMMUNICATIONS | 2021年 / 57卷 / 98期

基金：

美国国家卫生研究院;

关键词：

C-H FUNCTIONALIZATION; HECK-TYPE REACTIONS; ASYMMETRIC-SYNTHESIS; EFFICIENT; BONDS; ETHERS; BENZYL; ALLENAMIDES; OLEFINS;

D O I：

10.1039/d1cc05949a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An iron-catalysed C-H functionalisation of simple monosubstituted allenes for the synthesis of 1-tetrahydroisoquinolinyl 1,1-disubstituted allenes is reported. This transformation represents the first example of a direct conversion of allenic C-H bonds to C-C bonds through cross dehydrogenative coupling. The optimized protocol features broad scope and employs mild, functional group tolerant conditions.

引用

页码：13329 / 13332

页数：4

共 50 条

[1] Recent advances in iron-catalysed coupling reactions for the construction of the C(sp2)-C(sp2) bond
Chen, Peng
Chen, Hao-Nan
Wong, Henry N. C.
Peng, Xiao-Shui
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (30) : 6083 - 6095
[2] Iron-Catalyzed Contrasteric Functionalization of Allenic C(sp2)-H Bonds: Synthesis of α-Aminoalkyl 1,1-Disubstituted Allenes
Wang, Yidong
Scrivener, Sarah G.
Zuo, Xiao-Dong
Wang, Ruihan
Palermo, Philip N.
Murphy, Ethan
Durham, Austin C.
Wang, Yi-Ming
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (37) : 14998 - 15004
[3] Iron-Catalysed C(sp2)-H Borylation Enabled by Carboxylate Activation
Britton, Luke
Docherty, Jamie H.
Dominey, Andrew P.
Thomas, Stephen P.
[J]. MOLECULES, 2020, 25 (04):
[4] Iron-Catalysed C(sp2)-H Borylation with Expanded Functional Group Tolerance†
Britton, Luke
Docherty, Jamie H.
Nichol, Gary S.
Dominey, Andrew P.
Thomas, Stephen P.
[J]. CHINESE JOURNAL OF CHEMISTRY, 2022, 40 (24) : 2875 - 2881
[5] Iron-catalysed regioselective thienyl C–H/C–H coupling
Takahiro Doba
Laurean Ilies
Wataru Sato
Rui Shang
Eiichi Nakamura
[J]. Nature Catalysis, 2021, 4 : 631 - 638
[6] Iron-catalysed C(sp2)-H activation for aza-annulation with alkynes on extended π-conjugated systems
Zhang, Yan
Fukuma, Shota
Shang, Rui
Nakamura, Eiichi
[J]. NATURE SYNTHESIS, 2024,
[7] The direct α-C(sp3)-H functionalisation of N-aryl tetrahydroisoquinolines via an iron-catalysed aerobic nitro-Mannich reaction and continuous flow processing
Brzozowski, Martin
Forni, Jose A.
Savage, G. Paul
Polyzos, Anastasios
[J]. CHEMICAL COMMUNICATIONS, 2015, 51 (02) : 334 - 337
[8] Iron-catalysed C-3 functionalisation of indolizines via C-H bond cleavage
Xu Shao-hong
[J]. JOURNAL OF CHEMICAL RESEARCH, 2012, (08) : 441 - 443
[9] Iron-catalysed regioselective thienyl C-H/C-H coupling
Doba, Takahiro
Ilies, Laurean
Sato, Wataru
Shang, Rui
Nakamura, Eiichi
[J]. NATURE CATALYSIS, 2021, 4 (07) : 631 - 638
[10] Experimental and computational studies of the mechanism of iron-catalysed C-H activation/functionalisation with allyl electrophiles
DeMuth, Joshua C.
Song, Zhihui
Carpenter, Stephanie H.
Boddie, Theresa E.
Radovic, Aleksa
Baker, Tessa M.
Gutierrez, Osvaldo
Neidig, Michael L.
[J]. CHEMICAL SCIENCE, 2021, 12 (27) : 9398 - 9407

← 1 2 3 4 5 →