Synthesis of Isochromene and Related Derivatives by Rhodium-Catalyzed Oxidative Coupling of Benzyl and Allyl Alcohols with Alkynes

被引：83

作者：

Morimoto, Keisuke ^{[1
]}

Hirano, Koji ^{[1
]}

Satoh, Tetsuya ^{[1
]}

Miura, Masahiro ^{[1
]}

机构：

[1] Osaka Univ, Dept Appl Chem, Fac Engn, Suita, Osaka 5650871, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 22期

关键词：

C-H BOND; CARBON-HYDROGEN BONDS; INTERNAL ALKYNES; ACTIVATION; FUNCTIONALIZATION; CLEAVAGE; HETEROCYCLES; ARYLATION; ALKENES; ROUTE;

D O I：

10.1021/jo201923d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The straightforward synthesis of isochromene derivatives and related cyclic ethers is achieved by the rhodium-catalyzed oxidative coupling of alpha,alpha-disubstituted benzyl and allyl alcohols with alkynes. The hydroxy groups effectively act as the key function for the regioselective C-H bond cleavage.

引用

页码：9548 / 9551

页数：4

共 50 条

[41] Waste-Free Synthesis of Condensed Heterocyclic Compounds by Rhodium-Catalyzed Oxidative Coupling of Substituted Arene or Heteroarene Carboxylic Acids with Alkynes
Shimizu, Masaki
Hirano, Koji
Satoh, Tetsuya
Miura, Masahiro
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (09): : 3478 - 3483
[42] Rhodium-catalyzed selective cross-coupling of internal alkynes with a terminal silylacetylene
Katagiri, Takashi
Tsurugi, Hayato
Funayama, Atsushi
Satoh, Tetsuya
Miura, Masahiro
CHEMISTRY LETTERS, 2007, 36 (07) : 830 - 831
[43] Access to Coumarins by Rhodium-Catalyzed Oxidative Annulation of Aryl Thiocarbamates with Internal Alkynes
Zhao, Yingwei
Han, Feng
Yang, Lei
Xia, Chungu
ORGANIC LETTERS, 2015, 17 (06) : 1477 - 1480
[44] Comparison of "on water" and solventless procedures in the rhodium-catalyzed hydroformylation of diolefins, alkynes, and unsaturated alcohols
Alsalahi, W.
Trzeciak, A. M.
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2016, 423 : 41 - 48
[45] Synthesis of Spirocyclic Enones by Rhodium-Catalyzed Dearomatizing Oxidative Annulation of 2-Alkenylphenols with Alkynes and Enynes
Kujawa, Szymon
Best, Daniel
Burns, David J.
Lam, Hon Wai
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (28) : 8599 - 8602
[46] Rhodium-Catalyzed Cascade Annulative Coupling of 3,5-Diarylisoxazoles with Alkynes
Noguchi, Teppei
Nishii, Yuji
Miura, Masahiro
SYNTHESIS-STUTTGART, 2019, 51 (01): : 258 - 270
[47] RHODIUM-CATALYZED CROSS-COUPLING OF UNACTIVATED ALLENES AND 1-ALKYNES
YAMAGUCHI, M
OMATA, K
HIRAMA, M
TETRAHEDRON LETTERS, 1994, 35 (31) : 5689 - 5692
[48] Rhodium-catalyzed Annulative Coupling of Coumarin-3-Carboxylic Acids with Alkynes
Hayashi, Mikishiro
Komori, Kengo
Usuki, Yoshinosuke
Satoh, Tetsuya
CHEMISTRY LETTERS, 2023, 52 (05) : 307 - 309
[49] Synthesis of Siloles via Rhodium-Catalyzed Cyclization of Alkynes and Diynes with Hexamethyldisilane
Matsuda, Takanori
Suda, Yuya
Fujisaki, Yosuke
SYNLETT, 2011, (06) : 813 - 816
[50] Rhodium-catalyzed Synthesis of 1-Arylisoquinoline Derivatives through Annulative Coupling of 3-Aryl-1,2-benzisoxazoles and Alkynes
Noguchi, Teppei
Nishii, Yuji
Miura, Masahiro
CHEMISTRY LETTERS, 2017, 46 (10) : 1512 - 1514

← 1 2 3 4 5 →