Metal-free one-pot α-benzoxylation of benzylic alcohols with acids or aldehydes

被引：7

作者：

Zhu, Yefu

Zheng, Yong

Song, Weibin

Wei, Bole

Xuan, Lijiang ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, 501 Haike Rd,Zhangjiang Hitech Pk, Shanghai 201203, Peoples R China

来源：

TETRAHEDRON LETTERS | 2018年 / 59卷 / 04期

关键词：

nBu(4)NI; TBHP; alpha-Benzoxy ketones; Cross-dehydrogenative coupling; DEHYDROGENATIVE COUPLING CDC; TERT-BUTYL HYDROPEROXIDE; C-H BONDS; CARBOXYLIC-ACIDS; CARBONYL-COMPOUNDS; TRANSITION-METAL; EFFICIENT SYNTHESIS; ACETOXY KETONES; OXIDATION; ACYLATION;

D O I：

10.1016/j.tetlet.2017.12.030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A metal-free strategy has been developed for alpha-benzoxylation of benzylic alcohols with acids or aldehydes. The reaction proceeds via sequential oxidation and alpha-benzoxylation in one pot. Importantly, the reactions are performed in metal-free condition and utilize cheap aqueous TBHP as an oxidant, affording alpha-benzoxy ketones in moderate to good yields. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：368 / 371

页数：4

共 60 条

[1] Palladium-catalysed regioselective aroylation and acetoxylation of 3,5-diarylisoxazole via ortho C-H functionalisations [J].

Banerjee, Arghya ;

Bera, Anupam ;

Santra, Sourav Kumar ;

Guin, Srimanta ;

Patel, Bhisma K. .

RSC ADVANCES, 2014, 4 (17) :8558-8566

[2] Palladium-Catalyzed ortho-Aroylation of 2-Arylbenzothiazoles and 2-Arylbenzoxazoles with Aldehydes [J].

Banerjee, Arghya ;

Santra, Sourav Kumar ;

Guin, Srimanta ;

Rout, Saroj Kumar ;

Patel, Bhisma K. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (07) :1367-1376

[3] Direct coupling of indoles with carbonyl compounds: Short, enantioselective, gram-scale synthetic entry into the hapalindole and fischerindole alkaloid families [J].

Baran, PS ;

Richter, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (24) :7450-7451

[4] Pd-Catalyzed Ortho-C HAcylation/Cross Coupling of Aryl Ketone O-Methyl Oximes with Aldehydes Using tert-Butyl Hydroperoxide as Oxidant [J].

Chan, Chun-Wo ;

Zhou, Zhongyuan ;

Chan, Albert S. C. ;

Yu, Wing-Yiu .

ORGANIC LETTERS, 2010, 12 (17) :3926-3929

[5] Iron-Catalyzed Regioselective Direct Oxidative Aryl-Aryl Cross-Coupling [J].

Chandrasekharam, Malapaka ;

Chiranjeevi, Barreddi ;

Gupta, Kankatala S. V. ;

Sridhar, B. .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (24) :10229-10235

[6] Chemistry of acyl radicals [J].

Chatgilialoglu, C ;

Crich, D ;

Komatsu, M ;

Ryu, I .

CHEMICAL REVIEWS, 1999, 99 (08) :1991-2069

[7]

Cocker J. D., 1965, J CHEM SOC, P6

[8] Copper-Catalyzed Cross-Dehydrogenative Coupling (CDC) of Alkynes and Benzylic C-H Bonds [J].

Correia, Camille A. ;

Li, Chao-Jun .

ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (09) :1446-1450

[9] ELECTRONEGATIVELY SUBSTITUTED CARBOCATIONS [J].

CREARY, X .

CHEMICAL REVIEWS, 1991, 91 (08) :1625-1678

[10] Copper-catalyzed decarboxylative alkenylation of sp3 C-H bonds with cinnamic acids via a radical process [J].

Cui, Zili ;

Shang, Xiaojie ;

Shao, Xiang-Feng ;

Liu, Zhong-Quan .

CHEMICAL SCIENCE, 2012, 3 (09) :2853-2858

← 1 2 3 4 5 6 →