Direct Propargylation of ortho-Quinone Methides with Alkynyl Zinc Reagents: An Application to the One-Pot Synthesis of 2,3-Disubstituted Benzofurans

被引：3

作者：

Sun, Manman ^{[1
,2
]}

Song, Jinyu ^{[1
,2
]}

Wang, Lei ^{[3
]}

Yin, Wenguang ^{[3
]}

Miao, Maozhong ^{[3
]}

Ren, Hongjun ^{[1
,2
]}

机构：

[1] Taizhou Univ, Adv Res Inst, 1139 Shifu Ave, Taizhou 318000, Peoples R China

[2] Taizhou Univ, Dept Chem, 1139 Shifu Ave, Taizhou 318000, Peoples R China

[3] Zhejiang Sci Tech Univ, Dept Chem, Hangzhou 310018, Peoples R China

来源：

SYNLETT | 2020年 / 31卷 / 08期

关键词：

propargylation; ortho-quinone methides; alkynyl zinc reagents; benzofurans; TERMINAL ALKYNES; CONJUGATE ADDITION; ENANTIOSELECTIVE SYNTHESIS; CATALYZED 1,4-ADDITION; ALLYLIC ALKYLATION; NUCLEOPHILES; CYCLIZATION; ANNULATION; INDOLES; SYSTEM;

D O I：

10.1055/s-0039-1691739

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A transition-metal-free propargylation of ortho-quinone methides (o-QMs) with alkynyl zinc reagents was achieved. A conjugate alkynylation of an o-QM and subsequent cyclization sequence in the presence of KOt-Bu for the synthesis of 2,3-disubstituted benzofurans in one pot was developed. This efficient strategy exhibits good functional-group compatibility and gives moderate to good yields. The present reaction might serve as an attractive method for the synthesis of polysubstituted benzofurans.

引用

页码：818 / 822

页数：5

共 60 条

[1] Palladium-Catalyzed Synthesis of 2,3-Disubstituted Benzofurans: An Approach Towards the Synthesis of Deuterium Labeled Compounds [J].

Agasti, Soumitra ;

Maity, Soham ;

Szabo, Kalman J. ;

Maiti, Debabrata .

ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (10) :2331-2338

[2] Enantioselective copper-catalyzed conjugate addition and allylic substitution reactions [J].

Alexakis, A. ;

Backvall, J. E. ;

Krause, N. ;

Pamies, O. ;

Dieguez, M. .

CHEMICAL REVIEWS, 2008, 108 (08) :2796-2823

[3] The Domestication of ortho-Quinone Methides [J].

Bai, Wen-Ju ;

David, Jonathan G. ;

Feng, Zhen-Gao ;

Weaver, Marisa G. ;

Wu, Kun-Liang ;

Pettus, Thomas R. R. .

ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (12) :3655-3664

[4] Nickel-NHC-Catalyzed Cross-Coupling of 2-Methylsulfanylbenzofurans with Alkyl Grignard Reagents [J].

Baralle, Alexandre ;

Otsuka, Shinya ;

Guerin, Vincent ;

Murakami, Kei ;

Yorimitsu, Hideki ;

Osuka, Atsuhiro .

SYNLETT, 2015, 26 (03) :327-330

[5] The Emergence of Quinone Methides in Asymmetric Organocatalysis [J].

Caruana, Lorenzo ;

Fochi, Mariafrancesca ;

Bernardi, Luca .

MOLECULES, 2015, 20 (07) :11733-11764

[6] Catalytic and highly efficient 1,4-addition of terminal alkynes to conjugated enones by [RuCl2(p-cymene)]2/pyrrolidine [J].

Chang, S ;

Na, Y ;

Choi, E ;

Kim, S .

ORGANIC LETTERS, 2001, 3 (13) :2089-2091

[7] Synthesis of benzo[b]furans via CuI-catalyzed ring closure [J].

Chen, CY ;

Dormer, PG .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (17) :6964-6967

[8] The first palladium-catalyzed 1,4-addition of terminal alkynes to conjugated enones [J].

Chen, L ;

Li, CJ .

CHEMICAL COMMUNICATIONS, 2004, (20) :2362-2364

[9] A mild method for generation of o-quinone methides under basic conditions. The facile synthesis of trans-2,3-dihydrobenzofurans [J].

Chen, Mu-Wang ;

Cao, Liang-Liang ;

Ye, Zhi-Shi ;

Jiang, Guo-Fang ;

Zhou, Yong-Gui .

CHEMICAL COMMUNICATIONS, 2013, 49 (16) :1660-1662

[10]

Dell C P, 2001, SCI SYNTHESIS, V10, P11

← 1 2 3 4 5 6 →