Synthesis of Multisubstituted Allenes via Nickel-Catalyzed Cross-Electrophile Coupling

被引：37

作者：

Jin, Youxiang ^{[1
,2
]}

Wen, Hao ^{[1
,2
]}

Yang, Feiyan ^{[1
,2
]}

Ding, Decai ^{[1
,2
]}

Wang, Chuan ^{[1
,2
,3
]}

机构：

[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Hefei 230026, Anhui, Peoples R China

[2] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China

[3] Chinese Acad Sci, Ctr Excellence Mol Synth, Hefei 230026, Anhui, Peoples R China

来源：

ACS CATALYSIS | 2021年 / 11卷 / 21期

基金：

中国国家自然科学基金;

关键词：

allene; reductive cross-coupling; annulation; dicarbofunctionalization; nickel; ASYMMETRIC-SYNTHESIS; PROPARGYLIC CARBONATES; ALKYL-HALIDES; REDUCTIVE DICARBOFUNCTIONALIZATION; REGIOSELECTIVE SYNTHESIS; CYCLIZATION REACTIONS; ORGANOZINC REAGENTS; ARYL HALIDES; SUBSTITUTION; ESTERS;

D O I：

10.1021/acscatal.1c04143

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：

In this context, we report the successful application of a cross-electrophile strategy in the synthesis of multisubstituted allenes. Under the catalysis of nickel, reductive cross-coupling between propargyl carbonates and organoiodides provides an entry to prepare tri- or tetrasubstituted allenes without employing any pregenerated organometallics. Furthermore, propargyl carbonates also prove to be suitable allenylating agents in nickel-catalyzed asymmetric reductive aryl-allenylation of aryl-iodide-tethered unactivated alkenes, furnishing a variety of chiral benzene-fused cyclic compounds bearing a quaternary allenyl-substituted stereogenic center in a highly enantioselective manner.

引用

页码：13355 / 13362

页数：8

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