Pd-Catalyzed Cross-Coupling of Highly Sterically Congested Enol Carbamates with Grignard Reagents via C-O Bond Activation

被引：13

作者：

Chen, Zicong ^{[1
,2
]}

So, Chau Ming ^{[1
,2
,3
]}

机构：

[1] Hong Kong Polytech Univ, State Key Lab Chem Biol & Drug Discovery, Kowloon, Hong Kong, Peoples R China

[2] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, Kowloon, Hong Kong, Peoples R China

[3] Hong Kong Polytech Univ, Shenzhen Res Inst, Shenzhen, Peoples R China

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 10期

基金：

中国国家自然科学基金;

关键词：

PALLADIUM; ALKENYL; PHOSPHATES; TOSYLATES; COMPLEXES; TAMOXIFEN; EFFICIENT;

D O I：

10.1021/acs.orglett.0c01127

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The palladium-catalyzed cross-coupling reaction of enol carbamates to construct highly sterically congested alkenyl compounds is presented for the first time. This protocol demonstrates the potential of using thermally stable and highly atom-economic enol electrophiles as building blocks in bulky alkene synthesis. This reaction accommodates a broad substrate scope with excellent Z/E isomer ratios, which also provides a new synthetic pathway for accessing Tamoxifen.

引用

页码：3879 / 3883

页数：5

共 52 条

[1] Well-Defined Air-Stable Palladium HASPO Complexes for Efficient Kumada-Corriu Cross-Couplings of (Hetero)Aryl or Alkenyl Tosylates [J].

Ackermann, Lutz ;

Kapdi, Anant R. ;

Fenner, Sabine ;

Kornhaass, Christoph ;

Schulzke, Carola .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (10) :2965-2971

[2] Palladium-Catalyzed Direct Arylations, Alkenylations, and Benzylations through C-H Bond Cleavages with Sulfamates or Phosphates as Electrophiles [J].

Ackermann, Lutz ;

Barfuesser, Sebastian ;

Pospech, Jola .

ORGANIC LETTERS, 2010, 12 (04) :724-726

[3] Palladium- and Nickel-Catalyzed Alkenylation of Enolates [J].

Ankner, Tobias ;

Cosner, Casey C. ;

Helquist, Paul .

CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (06) :1858-1871

[4] Alkenylation of Arenes and Heteroarenes with Alkynes [J].

Boyarskiy, Vadim P. ;

Ryabukhin, Dmitry S. ;

Bokach, Nadezhda A. ;

Vasilyev, Aleksander V. .

CHEMICAL REVIEWS, 2016, 116 (10) :5894-5986

[5] Cross-Coupling and Related Reactions: Connecting Past Success to the Development of New Reactions for the Future [J].

Campeau, Louis-Charles ;

Hazari, Nilay .

ORGANOMETALLICS, 2019, 38 (01) :3-35

[6] Exploration of Aryl Phosphates in Palladium-Catalyzed Mono-α-arylation of Aryl and Heteroaryl Ketones [J].

Chen, Xiangmeng ;

Chen, Zicong ;

So, Chau Ming .

JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (10) :6337-6346

[7] Palladium-Catalyzed C(sp2)-N Bond Cross-Coupling with Triaryl Phosphates [J].

Chen, Zicong ;

Chen, Xiangmeng ;

So, Chau Ming .

JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (10) :6366-6376

[8] Percent buried volume for phosphine and N-heterocyclic carbene ligands: steric properties in organometallic chemistry [J].

Clavier, Herve ;

Nolan, Steven P. .

CHEMICAL COMMUNICATIONS, 2010, 46 (06) :841-861

[9] Selected patented cross-coupling reaction technologies [J].

Corbet, Jean-Pierre ;

Mignani, Gerard .

CHEMICAL REVIEWS, 2006, 106 (07) :2651-2710

[10] Designing Pd N-Heterocyclic Carbene Complexes for High, Reactivity and Selectivity for Cross-Coupling Applications [J].

Froese, Robert D. J. ;

Lombard, Christopher ;

Pompeo, Matthew ;

Rucker, Richard P. ;

Organ, Michael G. .

ACCOUNTS OF CHEMICAL RESEARCH, 2017, 50 (09) :2244-2253

← 1 2 3 4 5 6 →