Copper(i)-catalyzed 5-exo-trig radical cyclization/borylation of alkyl halides: access to functionalized pyrrolidine derivatives

2017 ◽  
Vol 15 (40) ◽  
pp. 8508-8512 ◽  
Author(s):  
Jie Cui ◽  
Hui Wang ◽  
Jian Song ◽  
Xiaochen Chi ◽  
Long Meng ◽  
...  
Keyword(s):  
Radical Cyclization ◽  
Alkyl Halides ◽  
One Step

This work reports the copper(i)-catalyzed 5-exo-trigradical cyclization/borylation of alkyl halides bearing an alkene moiety, during which a C–C bond and a C–B bond were formed in one step.

Intramolecular Radical Cyclization of Vinyl, Aryl and Alkyl Halides Using Catalytic Amount of Bis-tri-n-butyltin Oxide/Sodium Borohydride: A Novel Entry to Functionalized Carbocycles

Synlett ◽  
2015 ◽  
Vol 26 (08) ◽  
pp. 1055-1058 ◽  
Author(s):  
Namasivayam Palani ◽  
Sengottuvelan Balasubramanian ◽  
Tarur Dinesh
Keyword(s):  
Sodium Borohydride ◽  
Catalytic Amount ◽  
Radical Cyclization ◽  
Alkyl Halides ◽  
Cyclization Reactions

We wish to report a facile method in which a catalytic amount of bis-tri-n-butyltinoxide (TBTO) in the presence of sodium borohydride efficiently brings about the intramolecular radical cyclization of a variety of vinyl, aryl and alkyl halides to their corresponding functionalized bicyclic and tricyclic carbocycle frameworks. The methodology obviates the need for stoichiometric amounts of tin reagent normally required for radical cyclization reactions.

One-step conversion of protected alcohols into alkyl halides using dimethylphosgeniminium salt

1997 ◽  
Vol 38 (20) ◽  
pp. 3517-3520 ◽  
Author(s):  
T. Schlama ◽  
V. Gouverneur ◽  
C. Mioskowski
Keyword(s):  
Alkyl Halides ◽  
One Step

Tandem Radical Cyclizations: a One-Step Synthesis of Stereoisomeric Tricyclo[6.3.0.02,6]undecanes From Acyclic Precursors

1995 ◽  
Vol 48 (2) ◽  
pp. 261 ◽  
Author(s):  
DP Curran ◽  
SN Sun
Keyword(s):  
Radical Cyclization ◽  
Radical Cyclizations ◽  
Low Concentration ◽  
One Step

Radical cyclization of (1E,5Z)-1-iodoundeca-1,5,10-triene with triphenyltin hydride provides one acyclic, one monocyclic, two bicyclic and four tricyclic products. At low concentration (0.002 M), the title tricycloundecane products resulting from triple cyclization predominate, but the stereoselectivity is low. Cyclization of (1E,5Z)-1-iodo-8,8-bis( phenylsulfonyl )undeca-1,5,10-triene followed by reductive desulfonylation provides a similar ratio of products to the parent. The results show that this class of triple cyclization occurs well, but the level of stereoselectivity must be raised for it to become synthetically useful.

scholarly journals One-Step Synthesis of Acylboron Compounds via Cu-Catalyzed Carbonylative Borylation of Alkyl Halides

2020 ◽  
Author(s):  
Cheng Li-Jie ◽  
Zhao Siling ◽  
Neal Mankad
Keyword(s):  
Alkyl Halides ◽  
Efficient Synthesis ◽  
Mechanistic Studies ◽  
Acyl Halide ◽  
Reaction Conditions ◽  
One Pot ◽  
One Step ◽  
High Yields ◽  
Tertiary Alkyl

A Cu-catalyzed carbonylative borylation of unactivated alkyl halides has been developed, enabling efficient synthesis of aliphatic potassium acyltrifluoroborates (KATs) in high yields by treating the in-situ formed tetracoordinated acylboron intermediates with aqueous KHF2. A variety of functional groups are tolerated under the mild reaction conditions, and primary, secondary and tertiary alkyl halides are all applicable. In addition, this method also provides facile access to N-methyliminodiacetyl (MIDA) acylboronates as well as α-methylated potassium acyltrifluoroborates in a one-pot manner. Mechanistic studies indicate a radical atom transfer carbonylation (ATC) mechanism to form acyl halide intermediates that are subsequently borylated by (NHC)CuBpin.<br>

Cobalt-catalyzed radical cyclization of isocyanides forming phenanthridine derivatives

2018 ◽  
Vol 5 (20) ◽  
pp. 2997-3002 ◽  
Author(s):  
Xiangyu Liu ◽  
Chengjuan Wu ◽  
Jing Zhang ◽  
Yihan Shi ◽  
Shengnan Zhang ◽  
...  
Keyword(s):  
Radical Cyclization ◽  
Alkyl Halides

A neutral cobalt(ii) compound catalyzes the radical cyclization of 2-isocyano-biphenyls with various alkyl halides, providing a series of phenanthridine-fused polycycles.

Ligand-free Cu-catalyzed odorless synthesis of unsymmetrical sulfides through cross-coupling reaction of aryl/benzyl/alkyl halides with an aryl boronic acid/S8 system as a thiolating agent in PEG

RSC Advances ◽  
2015 ◽  
Vol 5 (46) ◽  
pp. 37060-37065 ◽  
Author(s):  
Abed Rostami ◽  
Amin Rostami ◽  
Arash Ghaderi ◽  
Mohammad Ali Zolfigol
Keyword(s):  
Boronic Acid ◽  
Coupling Reaction ◽  
Alkyl Halides ◽  
Green Solvent ◽  
Reaction Conditions ◽  
One Pot ◽  
Cross Coupling Reaction ◽  
Ligand Free ◽  
One Step ◽  
Aryl Boronic Acid

Efficient one-pot, one-step synthesis of unsymmetrical sulfides has been reported under mild reaction conditions with good yields in green solvent.

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