Here is a method for converting secondary and tertiary alcohols into the corresponding alkane using $\ce{InCl3}$ as a catalyst. Chlorodiphenylsilane is the only reagent used in addition to the catalyst. The method works in the presence of common functional groups leaving them untouched.
Since primary alcohols are unreactive, this reaction can be used to selectively reduce secondary and tertiary alcohols in their presence. An abstract showing a number of examples of the reaction can be found here.
Here is a method for converting secondary and tertiary alcohols into the corresponding alkane using $\ce{InCl3}$ as a catalyst. Chlorodiphenylsilane is the only reagent used in addition to the catalyst. The method works in the presence of common functional groups leaving them untouched.
Since primary alcohols are unreactive, this reaction can be used to selectively reduce secondary and tertiary alcohols in their presence. An abstract showing a number of examples of the reaction can be found here.
Red P + HI is a very strong reducing agent. It would reduce your alcohol to an alkane, but it might reduce other functional groups present as well. See earlier question for details.
Red P + HI is a very strong reducing agent. It would reduce your alcohol to an alkane, but it might reduce other functional groups present as well. See earlier question for details.
This is a very limited situation, but benzylic alcohols can be reduced to the corresponding alkyl group with simple hydrogenolysis conditions, hydrogen gas with Pd/C. This is similar to the cleavage of benzyl ethers, a common protecting group. Looking at it this way, the reaction deprotects water. An example of this reaction that I ran long ago is depicted below.
Developing a more general method for this transformation is an ongoing field of research, with many methods published. That often means that there isn't one single best method (yet). A 2013 publication from Li and coworkers used an iridium complex with hydrazine as the terminal oxidant. Benzylic, allylic, and notably primary alcohols were successfully reduced, although the benzylic/allylic substrates worked much better. The introduction offers a brief description on the state of the field: Iridium-Catalyzed Direct Dehydroxylation of Alcohols
This is a very limited situation, but benzylic alcohols can be reduced to the corresponding alkyl group with simple hydrogenolysis conditions, hydrogen gas with Pd/C. This is similar to the cleavage of benzyl ethers, a common protecting group. Looking at it this way, the reaction deprotects water. An example of this reaction that I ran long ago is depicted below.
Developing a more general method for this transformation is an ongoing field of research, with many methods published. That often means that there isn't one single best method (yet). A 2013 publication from Li and coworkers used an iridium complex with hydrazine as the terminal oxidant. Benzylic, allylic, and notably primary alcohols were successfully reduced, although the benzylic/allylic substrates worked much better. The introduction offers a brief description on the state of the field: Iridium-Catalyzed Direct Dehydroxylation of Alcohols
The following not catalytic and does not use hydrogen but tin hydrides:
Yes, it's the Barton-McCombie reaction.
If you don't mind a bit of photochemistry, use the method described by Isao Saito (DOI):
The following not catalytic and does not use hydrogen but tin hydrides:
Yes, it's the Barton-McCombie reaction.
If you don't mind a bit of photochemistry, use the method described by Isao Saito (DOI):
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Here is a method for converting secondary and tertiary alcohols into the corresponding alkane using $\ce{InCl3}$ as a catalyst. Chlorodiphenylsilane is the only reagent used in addition to the catalyst. The method works in the presence of common functional groups leaving them untouched.
Since primary alcohols are unreactive, this reaction can be used to selectively reduce secondary and tertiary alcohols in their presence. An abstract showing a number of examples of the reaction can be found here.
Here is a method for converting secondary and tertiary alcohols into the corresponding alkane using $\ce{InCl3}$ as a catalyst. Chlorodiphenylsilane is the only reagent used in addition to the catalyst. The method works in the presence of common functional groups leaving them untouched.
Since primary alcohols are unreactive, this reaction can be used to selectively reduce secondary and tertiary alcohols in their presence. An abstract showing a number of examples of the reaction can be found here.
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VOTE
Red P + HI is a very strong reducing agent. It would reduce your alcohol to an alkane, but it might reduce other functional groups present as well. See earlier question for details.
Red P + HI is a very strong reducing agent. It would reduce your alcohol to an alkane, but it might reduce other functional groups present as well. See earlier question for details.
More
VOTE
This is a very limited situation, but benzylic alcohols can be reduced to the corresponding alkyl group with simple hydrogenolysis conditions, hydrogen gas with Pd/C. This is similar to the cleavage of benzyl ethers, a common protecting group. Looking at it this way, the reaction deprotects water. An example of this reaction that I ran long ago is depicted below.
Developing a more general method for this transformation is an ongoing field of research, with many methods published. That often means that there isn't one single best method (yet). A 2013 publication from Li and coworkers used an iridium complex with hydrazine as the terminal oxidant. Benzylic, allylic, and notably primary alcohols were successfully reduced, although the benzylic/allylic substrates worked much better. The introduction offers a brief description on the state of the field: Iridium-Catalyzed Direct Dehydroxylation of Alcohols
This is a very limited situation, but benzylic alcohols can be reduced to the corresponding alkyl group with simple hydrogenolysis conditions, hydrogen gas with Pd/C. This is similar to the cleavage of benzyl ethers, a common protecting group. Looking at it this way, the reaction deprotects water. An example of this reaction that I ran long ago is depicted below.
Developing a more general method for this transformation is an ongoing field of research, with many methods published. That often means that there isn't one single best method (yet). A 2013 publication from Li and coworkers used an iridium complex with hydrazine as the terminal oxidant. Benzylic, allylic, and notably primary alcohols were successfully reduced, although the benzylic/allylic substrates worked much better. The introduction offers a brief description on the state of the field: Iridium-Catalyzed Direct Dehydroxylation of Alcohols
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