Organotellurium chemistry

Organotellurium chemistry in chemistry describes the synthesis and properties of chemical compounds containing a carbon to tellurium chemical bond.^[1] Organotellurium chemistry was developed in the wake of organoselenium chemistry and, sharing the same group in the periodic table, both chemistries have much in common. The field receives academic interest but organotellurium compounds rarely venture outside the laboratory. Dimethyl telluride is the only organotellurium compound that has been quantified in environmental samples.^[2]

Diphenyl ditelluride is used as a TePh source in organic synthesis. Dimethyl telluride as a product of microbial metabolism first discovered in 1939. it is used in Metalorganic vapour phase epitaxy. Commonly used tellurium based reagents are hydrogen telluride, NaHTe, sodium telluride, PhTeH and PhTeNa.

Reactions with these reagents are:

Organic reduction of aldehydes, alkenes, alkynes, nitro compounds, oxiranes to alkenes
Debromination of vicinal dibromides with E2 elimination
Organic oxidation of by compounds of the type (ArTeO)₂O
Tellurium tetrachloride reacts with alkenes and alkynes to the chloro tellurium trichloride addition product.
Tellurium in vinylic tellurium trichlorides can be replaced by halides with a variety of reagents (iodine, NBS )
Detellurative cross-coupling reaction: Compounds of the type Ar₂TeCl₂ engage in a coupling reaction to the corresponding biaryls with Raney nickel or palladium ^[3]

Another type is this Stille reaction ^[4]:

Hydrotelluration: Compounds of the type RTeH react with alkynes R'CCH to R'HCCTeR with anti addition to a Z-alkene. In contrast hydrostannylation, hydrozirconation and hydroalumination in similar reactions react with syn addition.
Te/Li exchange in transmetallation ^[5] is used in the synthesis of lithium reagents with demanding functional groups.
Allylic oxidation: like the selenium counterpart selenoxide oxidation, allylic telluroxides undergo [2,3]-sigmatropic rearrangements forming allylic alcohols after hydrolysis.
Olefin synthesis: Like the selenium counterpart selenoxide elimination, certain telluroxides (RTeOR) can form alkenes on heating.

CH				He
CLi	CBe	CB	CC	CN	CO	CF	Ne
CNa	CMg	CAl	CSi	CP	CS	CCl	CAr
CK	CCa	CSc	CTi	CV	CCr	CMn	CFe	CCo	CNi	CCu	CZn	CGa	CGe	CAs	CSe	CBr	CKr
CRb	CSr	CY	CZr	CNb	CMo	CTc	CRu	CRh	CPd	CAg	CCd	CIn	CSn	CSb	CTe	CI	CXe
CCs	CBa		CHf	CTa	CW	CRe	COs	CIr	CPt	CAu	CHg	CTl	CPb	CBi	CPo	CAt	Rn
Fr	Ra	Rf	Db	Sg	Bh	Hs	Mt	Ds	Rg	Cn	Uut	Uuq	Uup	Uuh	Uus	Uuo
	↓
	CLa	CCe	CPr	CNd	CPm	CSm	CEu	CGd	CTb	CDy	CHo	CEr	CTm	CYb	CLu
	Ac	Th	Pa	CU	Np	Pu	Am	Cm	Bk	Cf	Es	Fm	Md	No	Lr

**Chemical bonds to carbon**
Core organic chemistry	Many uses in chemistry
Academic research, but no widespread use	Bond unknown / not assessed

References

^ Organometallic Reagents for Synthetic Purposes: Tellurium Nicola Petragnani, and Wai-Ling Lo J. Braz. Chem. Soc., Vol. 9, No. 5, 415-425, 1998 http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50531998000500002.
^ Wallschläger, D.; Feldmann, F. (2010). Formation, Occurrence, Significance, and Analysis of Organoselenium and Organotellurium Compounds in the Environment. Metal Ions in Life Sciences. 7, Organometallics in Environment and Toxicology. RSC Publishing. pp. 319–364. ISBN 978-1-84755-177-1.
^ For an example see: Organic Syntheses, Coll. Vol. 6, p.468 (1988); Vol. 57, p.18 (1977). http://orgsynth.org/orgsyn/pdfs/CV6P0468.pdf
^ Palladium- and copper-catalyzed cross-coupling and carbonylative cross-coupling of organotellurium compounds with organostannanes (Chem. Commun. 1999, 2117) - Royal Society of Chemistry Suk-Ku Kang, Sang-Woo Lee and Hyung-Chul Ryu Link
^ For an example see: Organic Syntheses, Coll. Vol. 9, p.234 (1998); Vol. 72, p.154 (1995). http://orgsynth.org/orgsyn/pdfs/CV9P0234.pdf

CH																	He
CLi	CBe											CB	CC	CN	CO	CF	Ne
CNa	CMg											CAl	CSi	CP	CS	CCl	CAr
CK	CCa	CSc	CTi	CV	CCr	CMn	CFe	CCo	CNi	CCu	CZn	CGa	CGe	CAs	CSe	CBr	CKr
CRb	CSr	CY	CZr	CNb	CMo	CTc	CRu	CRh	CPd	CAg	CCd	CIn	CSn	CSb	CTe	CI	CXe
CCs	CBa		CHf	CTa	CW	CRe	COs	CIr	CPt	CAu	CHg	CTl	CPb	CBi	CPo	CAt	Rn
Fr	Ra		Rf	Db	Sg	Bh	Hs	Mt	Ds	Rg	Cn	Uut	Uuq	Uup	Uuh	Uus	Uuo
		↓
		CLa	CCe	CPr	CNd	CPm	CSm	CEu	CGd	CTb	CDy	CHo	CEr	CTm	CYb	CLu
		Ac	Th	Pa	CU	Np	Pu	Am	Cm	Bk	Cf	Es	Fm	Md	No	Lr

CH																	He
CLi	CBe											CB	CC	CN	CO	CF	Ne
CNa	CMg											CAl	CSi	CP	CS	CCl	CAr
CK	CCa	CSc	CTi	CV	CCr	CMn	CFe	CCo	CNi	CCu	CZn	CGa	CGe	CAs	CSe	CBr	CKr
CRb	CSr	CY	CZr	CNb	CMo	CTc	CRu	CRh	CPd	CAg	CCd	CIn	CSn	CSb	CTe	CI	CXe
CCs	CBa		CHf	CTa	CW	CRe	COs	CIr	CPt	CAu	CHg	CTl	CPb	CBi	CPo	CAt	Rn
Fr	Ra		Rf	Db	Sg	Bh	Hs	Mt	Ds	Rg	Cn	Uut	Uuq	Uup	Uuh	Uus	Uuo
		↓
		CLa	CCe	CPr	CNd	CPm	CSm	CEu	CGd	CTb	CDy	CHo	CEr	CTm	CYb	CLu
		Ac	Th	Pa	CU	Np	Pu	Am	Cm	Bk	Cf	Es	Fm	Md	No	Lr

Organotellurium chemistry

See also

References

CH																	He
CLi	CBe											CB	CC	CN	CO	CF	Ne
CNa	CMg											CAl	CSi	CP	CS	CCl	CAr
CK	CCa	CSc	CTi	CV	CCr	CMn	CFe	CCo	CNi	CCu	CZn	CGa	CGe	CAs	CSe	CBr	CKr
CRb	CSr	CY	CZr	CNb	CMo	CTc	CRu	CRh	CPd	CAg	CCd	CIn	CSn	CSb	CTe	CI	CXe
CCs	CBa		CHf	CTa	CW	CRe	COs	CIr	CPt	CAu	CHg	CTl	CPb	CBi	CPo	CAt	Rn
Fr	Ra		Rf	Db	Sg	Bh	Hs	Mt	Ds	Rg	Cn	Uut	Uuq	Uup	Uuh	Uus	Uuo
		↓
		CLa	CCe	CPr	CNd	CPm	CSm	CEu	CGd	CTb	CDy	CHo	CEr	CTm	CYb	CLu
		Ac	Th	Pa	CU	Np	Pu	Am	Cm	Bk	Cf	Es	Fm	Md	No	Lr