Rhodium-Catalyzed Regio- and Diastereoselective Hydroarylation of Allenes: An Unprecedented Ene Reaction

被引：6

作者：

Ghazvini, Helya J. ^{[1
,2
]}

Khosravi, Hormoz ^{[1
,2
]}

Mirzaei, Saber ^{[3
]}

Balalaie, Saeed ^{[2
,4
]}

Breit, Bernhard ^{[1
]}

机构：

[1] Albert Ludwigs Univ Freiburg, Inst Organ Chem, D-79104 Freiburg, Germany

[2] KN Toosi Univ Technol, Peptide Chem Res Ctr, Tehran 1541849611, Iran

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

[4] Kermanshah Univ Med Sci, Med Biol Res Ctr, Kermanshah 6714967346, Iran

来源：

ACS CATALYSIS | 2021年 / 11卷 / 23期

关键词：

rhodium; isocyanide; allene; hydroarylation; nucleophilic addition; tandem reaction; heterocycle; C-H ACTIVATION; INTRAMOLECULAR HYDROARYLATION; ALPHA-ISOCYANOACETAMIDES; ISOCYANIDES; FUNCTIONALIZATIONS; ALLYLATION;

D O I：

10.1021/acscatal.1c04743

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A rhodium-catalyzed nucleophilic addition of alpha-acidic isocyanoacetamides to allenes for the selective formation of Z-vinyl-functionalized oxazoles as an unprecedented method for hydroarylation of allenes is described. Employing diverse isocyanoacetamides and allenes, a library of vinyl oxazoles is introduced in a stereo- and regiospecific fashion and moderate to high yields. Mechanistic investigations reveal that the reaction proceeds through a concise rhodium-catalyzed ene reaction followed by reductive elimination.

引用

页码：14570 / 14574

页数：5

共 42 条

[1] Ackermann L, 2018, CATALYTIC HYDROARYLATION OF CARBON-CARBON MULTIPLE BONDS, P1
[2] Rhodium-catalyzed asymmetric intramolecular hydroarylation of allenes: access to functionalized benzocycles
Berthold, Dino
Klett, Johannes
Breit, Bernhard
[J]. CHEMICAL SCIENCE, 2019, 10 (43) : 10048 - 10052
[3] Stereospecific Synthesis of 1,4,5,6-Tetrahydropyrimidines via Domino Ring-Opening Cyclization of Activated Aziridines with α-Acidic Isocyanides
Bhattacharyya, Aditya
Shahi, Chandan Kumar
Pradhan, Sajan
Ghorai, Manas K.
[J]. ORGANIC LETTERS, 2018, 20 (10) : 2925 - 2928
[4] Alkenylation of Arenes and Heteroarenes with Alkynes
Boyarskiy, Vadim P.
Ryabukhin, Dmitry S.
Bokach, Nadezhda A.
Vasilyev, Aleksander V.
[J]. CHEMICAL REVIEWS, 2016, 116 (10) : 5894 - 5986
[5] Base Metal Catalyzed Isocyanide Insertions
Collet, Jurrien W.
Roose, Thomas R.
Ruijter, Eelco
Maes, Bert U. W.
Orru, Romano V. A.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (02) : 540 - 558
[6] Transition-Metal-Catalyzed C-H Alkylation Using Alkenes
Dong, Zhe
Ren, Zhi
Thompson, Samuel J.
Xu, Yan
Dong, Guangbin
[J]. CHEMICAL REVIEWS, 2017, 117 (13) : 9333 - 9403
[7] Synthesis of polysubstituted 4,5,6,7-tetrahydrofuro[2,3-c]pyridines by a novel multicomponent reaction
Fayol, A
Zhu, JP
[J]. ORGANIC LETTERS, 2004, 6 (01) : 115 - 118
[8] Fayol A, 2002, ANGEW CHEM INT EDIT, V41, P3633, DOI 10.1002/1521-3773(20021004)41:19<3633::AID-ANIE3633>3.0.CO
[9] 2-T
[10] 1,6-Addition Arylation of para-Quinone Methides: An Approach to Unsymmetrical Triarylmethanes
Gao, Shang
Xu, Xiuyan
Yuan, Zhenbo
Zhou, Haipin
Yao, Hequan
Lin, Aijun
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (17) : 3006 - 3012

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