Nickel-Catalyzed Negishi Cross-Coupling of Alkyl Halides, Including Unactivated Tertiary Halides, with a Boron-Stabilized Organozinc Reagent

被引：9

作者：

Guo, Panchi ^{[1
]}

Jin, Hao ^{[1
]}

Han, Jinhui ^{[1
]}

Xu, Liang ^{[2
]}

Li, Pengfei ^{[3
]}

Zhan, Miao ^{[1
]}

机构：

[1] Northwestern Polytech Univ, Inst Med Res, Xian Key Lab Stem Cell & Regenerat Med, Xian 710072, Shaanxi, Peoples R China

[2] Shihezi Univ, Sch Chem & Chem Engn, Key Lab Green Proc Chem Engn Xinjiang Bingtuan, Shihezi 832003, Peoples R China

[3] Xi An Jiao Tong Univ, Frontier Inst Sci & Technol, Xian 710054, Peoples R China

来源：

ORGANIC LETTERS | 2023年

基金：

中国国家自然科学基金;

关键词：

GRIGNARD-REAGENTS; SECONDARY; CARBON; NI; ELECTROPHILES; NUCLEOPHILES; PALLADIUM; BROMIDES;

D O I：

10.1021/acs.orglett.3c00051

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nickel-catalyzed cross-coupling of unactivated tertiary alkyl electrophiles with alkylmetal reagents is still a challenge. We report herein a nickel-catalyzed Negishi cross-coupling of alkyl halides, including unactivated tertiary halides, with boron-stabilized organozinc reagent BpinCH(2)ZnI, yielding versatile organoboron products with high functional-group tolerance. Importantly, the Bpin group was found to be indispensable for accessing the quaternary carbon center. The synthetic practicability of the prepared quaternary organoboronates was demonstrated by their conversion to other useful compounds.

引用

页码：1268 / 1273

页数：6

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