Nickel-Catalyzed C(sp3)-C(sp3) Cross-Electrophile Coupling of InSitu Generated NHP Esters with Unactivated Alkyl Bromides

被引：36

作者：

Kang, Kai ^{[1
]}

Weix, Daniel J. ^{[1
]}

机构：

[1] Univ Wisconsin, Madison, WI 53706 USA

来源：

ORGANIC LETTERS | 2022年 / 24卷 / 15期

关键词：

REDOX-ACTIVE ESTERS; HALIDES; OXIDATION; DECARBOXYLATION; NI;

D O I：

10.1021/acs.orglett.2c00805

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The formation of C(sp3)-C(sp3) bonds by cross-coupling remains a challenge in synthesis. Here, we demonstrate atwo-step, one-pot protocol for the in situ generation ofN-hydroxyphthalimide esters and their nickel-catalyzed cross-electrophilecoupling with unactivated alkyl bromides for the construction of 1 degrees/1 degrees C(sp3)-C(sp3) bonds. The conditions tolerate an array of functionalgroups, and mechanistic studies indicate that both substrates areconverted to alkyl radicals during the reaction.

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页码：2853 / 2857

页数：5

相关论文

共 69 条

[1]

Albini A., 2010, HDB SYNTHETIC PHOTOC, P13

[2] Aerobic oxidation of benzyl alcohols catalyzed by aryl substituted N-hydroxyphthalimides.: Possible involvement of a charge-transfer complex [J].

Annunziatini, C ;

Gerini, MF ;

Lanzalunga, O ;

Lucarini, M .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (10) :3431-3438

[3] New mediators for the enzyme laccase: mechanistic features and selectivity in the oxidation of non-phenolic substrates [J].

Astolfi, P ;

Brandi, P ;

Galli, C ;

Gentili, P ;

Gerini, MF ;

Greci, L ;

Lanzalunga, O .

NEW JOURNAL OF CHEMISTRY, 2005, 29 (10) :1308-1317

[4] Mechanism and Selectivity in Nickel-Catalyzed Cross-Electrophile Coupling of Aryl Halides with Alkyl Halides [J].

Biswas, Soumik ;

Weix, Daniel J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (43) :16192-16197

[5] Organic synthesis provides opportunities to transform drug discovery [J].

Blakemore, David C. ;

Castro, Luis ;

Churcher, Ian ;

Rees, David C. ;

Thomas, Andrew W. ;

Wilson, David M. ;

Wood, Anthony .

NATURE CHEMISTRY, 2018, 10 (04) :383-394

[6] Deoxygenation of Ethers To Form Carbon-Carbon Bonds via Nickel Catalysis [J].

Cao, Zhi-Chao ;

Shi, Zhang-Jie .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (19) :6546-6549

[7] Advances in functional-group-tolerant metal-catalyzed alkyl-alkyl cross-coupling reactions [J].

Cárdenas, DJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (04) :384-387

[8] Nickel-Catalyzed Reductive Allylation of Tertiary Alkyl Halides with Allylic Carbonates [J].

Chen, Haifeng ;

Jia, Xiao ;

Yu, Yingying ;

Qian, Qun ;

Gong, Hegui .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (42) :13103-13106

[9] Catalytic alkylation of unactivated C(sp3)-H bonds for C(sp3)-C(sp3) bond formation [J].

Chen, Zhen ;

Rong, Meng-Yu ;

Nie, Jing ;

Zhu, Xue-Feng ;

Shi, Bing-Feng ;

Ma, Jun-An .

CHEMICAL SOCIETY REVIEWS, 2019, 48 (18) :4921-4942

[10] Transition metal-catalyzed alkyl-alkyl bond formation: Another dimension in cross-coupling chemistry [J].

Choi, Junwon ;

Fu, Gregory C. .

SCIENCE, 2017, 356 (6334)

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