Addition of Dissimilar Carbenes across an Unsymmetrically Substituted Alkyne: Regio- and Stereoselective Synthesis of Trisubstituted 1,3-Dienes

被引：8

作者：

O'Connor, Joseph M. ^{[1
]}

Chen, Ming-Chou ^{[1
,2
]}

Holland, Ryan L. ^{[1
]}

Rheingold, Arnold L. ^{[1
]}

机构：

[1] Univ Calif San Diego, Dept Chem & Biochem 0358, La Jolla, CA 92093 USA

[2] Natl Cent Univ, Dept Chem, Chungli 32054, Taiwan

来源：

ORGANOMETALLICS | 2011年 / 30卷 / 03期

基金：

美国国家科学基金会;

关键词：

METALLACYCLOBUTENE COMPLEX; COBALT COMPLEX; ISOMERIZATION; DIENES;

D O I：

10.1021/om1007314

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The formal addition of dissimilar carbenes across an unsymmetrically substituted alkyne has been achieved for the first time by a two-step sequence in which a cobalt alkyne complex undergoes reaction with a carbene addend (CHR1) to give a metallacyclobutene complex, followed by reaction with a second carbene addend (CHR2) to give a mixture of diene complexes. In situ treatment of the diene mixture with fluoride leads to desilylation and conversion to a single cobalt diene complex with a high degree of regio- and stereoselectivity.

引用

页码：369 / 371

页数：3

共 19 条

[1] Envelope-flip dynamics in CpCo(diene) complexes: an ab initio quantum mechanical study [J].

Baldridge, KK ;

O'Connor, JM ;

Chen, MC ;

Siegel, JS .

JOURNAL OF PHYSICAL CHEMISTRY A, 1999, 103 (49) :10126-10131

[2] 1ST PHOTOCHEMICAL ENVELOPE ISOMERIZATION OF A LATE-TRANSITION-METAL 1,3-BUTADIENE COMPLEX - A TRIPLE STEREOCHEMICAL LABELING EXPERIMENT [J].

EATON, B ;

KING, JA ;

VOLLHARDT, KPC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (06) :1359-1360

[3] ORGANO-IRON COMPLEXES .4. REACTIONS OF SUBSTITUTED DIENES WITH IRON PENTACARBONYL [J].

EMERSON, GF ;

PETTIT, R ;

KOCHHAR, R ;

MAHLER, JE .

JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (12) :3620-&

[4] AN UNPRECEDENTED PROPELLANE-TO-SPIROFUSED SKELETAL REARRANGEMENT UPON OXIDATIVE DEMETALATION OF CPCO-COMPLEXED POLYCYCLIC DIENES - SYNTHESIS OF A PENTACYCLIC, POTENTIAL PRECURSOR TO STRYCHNINE [J].

GROTJAHN, DB ;

VOLLHARDT, KPC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (14) :5653-5654

[5] Reactions of a metallacyclobutene complex with alkenes [J].

Holland, Ryan L. ;

Bunker, Kevin D. ;

Chen, Christopher H. ;

DiPasquale, Antonio G. ;

Rheingold, Arnold L. ;

Baldridge, Kim K. ;

O'Connor, Joseph M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (31) :10093-+

[6] Nitroso Compounds Serve as Precursors to Late-Metal η2(N,O)-Hydroxylamido Complexes [J].

Holland, Ryan L. ;

O'Connor, Joseph M. .

ORGANOMETALLICS, 2009, 28 (02) :394-396

[7] REACTION OF A DIPHENYLACETYLENE-COBALT COMPLEX WITH ALKYL DIAZOACETATES [J].

HONG, P ;

AOKI, K ;

YAMAZAKI, H .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1978, 150 (02) :279-293

[8] THE THERMALLY-INDUCED PROTOTROPIC ISOMERIZATION OF ETA-4-1,3-DIALKENES, ETA-4-1,4-DIALKENES, ETA-4-1,5-DIALKENES COMPLEXED TO (ETA-5-CYCLOPENTADIENYL)COBALT [J].

KING, JA ;

VOLLHARDT, KPC .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1993, 460 (01) :91-96

[9] Catalytic double addition of diazo compounds to alkynes:: Synthesis of functional conjugated dienes [J].

Le Paih, J ;

Dérien, S ;

Özdemir, I ;

Dixneuf, PH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (30) :7400-7401

[10] Ruthenium-Catalyzed Synthesis of Functional Conjugated Dienes via Addition of Two Carbene Units to Alkynes [J].

Le Paih, Jacques ;

Vovard-Le Bray, Chloe ;

Derien, Sylvie ;

Dixneuf, Pierre H. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (21) :7391-7397

← 1 2 →