Titanium: A Unique Metal for Radical Dehydroxylative Functionalization of Alcohols

被引：16

作者：

Pang, Xiaobo ^{[1
]}

Shu, Xing-Zhong ^{[1
]}

机构：

[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem SKLAOC, 222 South Tianshui Rd, Lanzhou 730000, Peoples R China

来源：

SYNLETT | 2021年 / 32卷 / 13期

基金：

中国国家自然科学基金;

关键词：

titanium; alcohols; radical; dehydroxylation; reductive coupling;

D O I：

10.1055/a-1406-0484

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The dehydroxylative functionalization of alcohols is synthetic appealing, but it remains a long-term challenge in the synthetic community. Low-valent titanium has shown the power to produce carbon radicals from alcohols via homolytic cleavage of the C-OH bonds and thus offers the potential to overcome this problem. In this perspective manuscript, we summarized the recent advance on radical dehydroxylative transformation of alcohols either promoted or catalyzed by titanium. The limitation and outlook of the studies in this field are also provided.

引用

页码：1269 / 1274

页数：6

共 46 条

[1]

Baridari, 2020, J ORG CHEM, V85, P3320

[2] FORMATION OF QUATERNARY CARBON CENTERS FROM TERTIARY ALCOHOLS BY FREE-RADICAL METHODS [J].

BARTON, DHR ;

CRICH, D .

TETRAHEDRON LETTERS, 1985, 26 (06) :757-760

[3] Modern applications of low-valent early transition metals in synthesis and catalysis [J].

Beaumier, Evan P. ;

Pearce, Adam J. ;

See, Xin Yi ;

Tonks, Ian A. .

NATURE REVIEWS CHEMISTRY, 2019, 3 (01) :15-34

[4]

Bermudez E, 2002, TOXICOL, V70

[5] Mechanistic Insights into the ReIO2(PPh3)2-Promoted Reductive Coupling of Alcohols [J].

Boucher-Jacobs, Camille ;

Liu, Peng ;

Nicholas, Kenneth M. .

ORGANOMETALLICS, 2018, 37 (15) :2468-2480

[6]

Cahours MA., 1861, ANN CHIM PHYS, V62, P257

[7]

Castro-Rodriguez M., 2017, Org. Process Res. Dev., V21, P911, DOI DOI 10.1021/acs.oprd.7b00098

[8] C-O bond homolysis in a tungsten alkoxide: The mechanism of alcohol deoxygenation by WCl2(PMe3)(4) and WH2Cl2(PMe3)(4) [J].

Crevier, TJ ;

Mayer, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (36) :8485-8491

[9] METAL SIGMA-HYDROCARBYLS, MR NORMAL-STOICHIOMETRY, STRUCTURES, STABILITIES, AND THERMAL-DECOMPOSITION PATHWAYS [J].

DAVIDSON, PJ ;

LAPPERT, MF ;

PEARCE, R .

CHEMICAL REVIEWS, 1976, 76 (02) :219-242

[10] Weakening C-O Bonds: Ti(III), a New Reagent for Alcohol Deoxygenation and Carbonyl Coupling Olefination [J].

Dieguez, Horacio R. ;

Lopez, Armando ;

Domingo, Victoriano ;

Arteaga, Jesus F. ;

Dobado, Jose A. ;

Herrador, M. Mar ;

Quilez del Moral, Jose F. ;

Barrero, Alejandro F. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (01) :254-259

← 1 2 3 4 5 →